Fischer Indole Synthesis in Low Melting Mixtures
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- Γιάννη Γιαννόπουλος
- 6 χρόνια πριν
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1 Fischer Indole Synthesis in Low Melting Mixtures Sangram Gore, a,b Sundarababu Baskaran* a and Burkhard König* b Supporting Information Table of Contents: General Information General Procedure for the formation of indoles Characterization data for compounds Copy of 1 H and 13 C MR spectra of compounds S2 S2 S2-S10 S11-S127 S1
2 General Information 1 H MR spectra were recorded on Bruker ADVACE 400 MHz and 500 MHz spectrometers. 13 C MR spectra were recorded on 100 MHz and 125 MHz spectrometers. Chemical shifts are expressed in δ units relative to tetramethylsilane (TMS) signal as internal reference in CDCl 3. FTIR spectra were recorded in CHCl 3 or neat. Column chromatography was performed on silica gel ( mesh) using ethyl acetate and hexane as eluent. General Procedure for the preparation of indole derivatives: In a typical experiment, 1.5 g of L-(+)-tartaric acid-dmu (30:70) mixture was heated to 70 o C to obtain a clear melt. To this melt, 1 mmol of aryl hydrazine.hcl and 1 mmol of aldehyde/ketone were added at 70 o C. The reaction was monitored by thin layer chromatography. After completion, the reaction mixture was quenched by adding water while still hot. The reaction mixture was cooled to room temperature and the solid that separated was filtered and washed with water (2 x 5 ml). The crude compound was dried under vacuum and recrystallized from ethanol to afford pure product. In case of liquid products, the reaction mixture was quenched with water and the aqueous layer was extracted with DCM (3 x 5 ml). The organic layer was washed with water (2 x 5 ml), dried over anhydrous a 2 SO 4 and concentrated under reduced pressure. The crude compound was purified by column chromatography over silica gel. Experimental Section Spectral data for the indole derivatives obtained by the Fischer indole reaction between aldehyde/ketone and aryl hydrazine in tartaric acid-dmu melt: 3a. 2,3,4,9-Tetrahydro-1H-carbazole: H Colorless solid; Yield 97%; M.p o C; IR (neat): 3396, 1455, 739 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), (m, 4H), (m, 2H), 7.18 (dd, 1H, J = 7.6, 1.6 Hz) 7.38 (d, 1H, J = 7.6 Hz), 7.55 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 21.0, 23.3, 23.4, 110.3, 110.5, 117.8, 119.2, 121.1, 128.0, 134.2, b. 5,6,7,8,9,10-Hexahydrocyclohepta[b]indole: H Colorless solid; Yield 98%; M.p o C; IR (neat): 3388, 1456, 741 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), (m, 2H), 2.80 (t, 4H, J = 5.6 Hz), (m, 2H), (m, 1H), (m, 1H), 7.62 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 24.8, 27.6, 28.8, 29.7, 31.9, 110.3, 113.8, 117.7, 119.1, 120.7, 129.3, 134.3, 137.5; HRMS calcd. for C 13 H 16 1 (M + +1) , found S2
3 3c. 6,7,8,9,10,11-Hexahydro-5H-cycloocta[b]indole: H Colorless solid; Yield 96%; M.p o C; IR (neat): 3329, 1623, 1453, 1334, 742 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), (m, 4H), (m, 4H), (m, 2H), (m, 1H), (m, 1H), 7.63 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 22.3, 26.0, 26.1, 29.6, 29.7, 110.4, 111.8, 117.8, 119.0, 120.7, 128.7, 135.1, 135.7; HRMS calcd. for C 14 H 18 1 (M + +1) , found d. 1,2,3,4-Tetrahydrocyclopenta[b]indole: H Colorless solid; Yield 97%; M.p o C; IR (neat): 3399, 1654, 1609, 1405, 1233, 741 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 4H), (m, 2H), (m, 1H), (m, 1H), 7.82 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 24.6, 26.0, 28.8, 111.4, 118.6, 119.6, 119.9, 120.6, 124.9, 141.1, 143.8; HRMS calcd. for C 11 H 12 1 (M + +1) , found e. 2,3-Dimethyl-1H-indole: Me H Colorless solid; Yield 88%; M.p o C; IR (neat): 3396, 1467, 740 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 2.12 (s, 3H), 2.20 (s, 3H), (m, 2H), (m, 1H), (m, 2H); 13 C MR (100 MHz, CDCl 3 ): δ 8.5, 11.6, 107.1, 110.2, 118.0, 119.1, 121.0, 129.5, 130.8, 135.3; HRMS calcd. for C 10 H 12 1 (M + +1) , found Me 3f. 3-Phenyl-1H-indole: Ph H Colorless solid; Yield 87%; M.p o C; IR (neat): 3405, 3048, 1597, 1451, 1111, 741, 694 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 3H), 7.33 (d, 1H, J = 2.8 Hz), (m, 3H), (m, 2H), 7.95 (d, 1H, J = 7.6 Hz), 8.19 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 111.5, 118.5, 119.9, 120.4, 121.9, 122.5, 125.9, 126.1, 127.6, 128.9, 135.7, 136.8; HRMS calcd. for C 14 H 12 (M + +1) , found S3
4 3g. Tert-butyl 3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate: Boc H Pale yellow oil; Yield 85%; IR (neat): 3317, 1686, 1405, 1152, 753 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.53 (s, 9H), 2.81 (t, 2H, J = 5.6 Hz), 3.83 (s, 2H), 4.67 (s, 2H), (m, 2H), 7.31 (d, 1H, J = 7.6 Hz), 7.46 (br s, 1H), 8.15 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 23.6, 28.5, 28.6, 40.8, 41.6, 80.1, 107.5, 110.9, 117.6, 119.6, 121.6, 125.7, 128.4, 131.8, 132.3, 136.0, 155.4; HRMS calcd. for C 16 H 21 2 O 2 (M + +1) , found h. Benzyl 3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate: Cbz H Colorless oil; Yield 94%; IR (neat): 3315, 1684, 1615, 1425, 1219, 731 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 2.85 (s, 2H), 3.90 (d, 2H, J = 5.2 Hz), 4.75 (s, 2H), 5.22 (s, 2H), (m, 2H), (m, 7H), 8.0 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 23.5, 23.8, 41.5, 67.4, 107.1, 110.9, 117.7, 119.7, 121.8, 128.1, 128.2, 128.5, 128.6, 132.0, 136.0, 136.8, 156.1; HRMS calcd. for C 19 H 19 2 O 2 (M + +H) , found i. 5,10-Dihydroindeno[1,2-b]indole: H Colorless solid; Yield 97%; M.p o C; IR (neat): 3404, 1446, 737 cm -1 ; 1 H MR (400 MHz, MeOD): δ (m, 2H), (m, 2H) (m, 1H), 6.95 (dd, 1H, J = 12.8, 5.6 Hz), 7.06 (d, 1H, J = 8.0 Hz), (m, 3H); 13 C MR (100 MHz, MeOD): δ 30.8, 113.1, 118.5, 119.4, 120.5, 121.5, 122.1, 125.6, 125.9, 126.3, 127.5, 136.8, 149.1, 145.0, 142.5; HRMS calcd. for C 15 H 12 1 (M + +1) , found j. 3-Methyl-2-phenyl-1H-indole: CH 3 H Ph S4
5 Colorless solid; Yield 97%; M.p o C; IR (neat): 3337, 3054, 1607, 1583, 1536, 1449, 1265 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 2.35 (s, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), 7.50 (d, 1H, J = 7.6 Hz), 7.83 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 9.8, 108.8, 110.8, 119.1, 119.6, 122.4, 127.4, 127.8, 128.9, 130.2, 133.5, 134.1, 136.0; HRMS calcd. for C 15 H 14 (M + +H) , found k. 3-Isopropyl-2-methyl-1H-indole: H 3 C CH 3 H Yellow oil; Yield 95%; IR (neat): 3392, 2963, 1608, 1462, 1022 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.40 (d, 6H, J = 7.2 Hz), 2.35 (s, 3H), 3.17 (sep, 1H, J = 7.2 Hz), (m, 2H), 7.22 (d, 1H, J = 7.2 Hz), 7.58 (s, 1H), 7.65 (d, 1H, J = 7.2 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 12.2, 23.1, 26.0, 110.4, 117.9, 118.8, 119.5, 120.6, 127.5, 129.3, 135.5; HRMS calcd. for C 12 H 16 (M + +1) , found l. 3-(1H-Indol-3-yl)propan-1-ol: CH 3 OH H Yellow oil; Yield 80%; IR (neat): , 1457, 1024, 741 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (quin, 2H, J = 6.4 Hz ), 2.86 (t, 2H, J = 7.6 Hz), 3.73 (t, 2H, J = 6.4 Hz), 6.99 (s, 1H), (m, 1H), (m, 1H), 7.35 (d, 1H, J = 8.0 Hz), 7.62 (d, 1H, J = 8.0 Hz), 8.0 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 21.5, 33.0, 62.8, 111.2, 116.0, 119.0, 119.3, 121.4, 122.1, 127.6, 136.5; HRMS calcd. for C 11 H 14 O (M + +1) , found m. 2-(1H-Indol-3-yl)ethanol: H Colorless oil; Yield 90%; IR (neat): , 1660, 1493, 1282, 1034 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 3.05 (t, 2H, J = 6.0 Hz), 3.92 (t, 2H, J = 6.4 Hz), (m, 2H), (m, 1H), 7.38 (d, 1H, J = 8.4 Hz), 7.63 (d, 1H, J = 7.6 Hz), 8.10 (br s, 1H); 13 C MR (125 MHz, CDCl 3 ): δ 28.8, 62.6, 111.2, 112.3, 118.9, 119.5, 122.2, 122.5, 127.4, 136.5; HRMS calcd. for C 10 H 12 O (M + +H) , found OH S5
6 3n. (S)-Dimethyl 2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)malonate: H CO 2 Me CO 2 Me Colorless solid; Yield 97%; [α] 20 D = (c 1.0, CHCl 3 ); M.p o C; IR (neat): , 2932, 1564, 1039 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 1H), (m, 1H), (m, 5H), 3.41 (d, 1H, J = 8.8 Hz, CH(COOCH 3 ) 2 ), 3.68 (s, 3H, COOCH 3 ), 3.70 (s, 3H, COOCH 3 ), (m, 2H), 7.17 (d, 1H, J = 8.0 z), 7.37 (d, 1H, J = 7.6 Hz), 7.65 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 20.1, 27.1, 27.6, 34.8, 52.6 (COOCH 3 ), 52.7 (COOCH 3 ), 56.5 (CH(COOCH 3 ) 2 ), 109.5, 110.6, 117.9, 119.3, 121.3, 127.4, 132.4, 136.0, (C=O), (C=O); HRMS calcd. for C 17 H 23 2 O 3 (M + +a): , found o. 6,7,8,9,10,11-Hexahydro-5H-cycloocta[b]indole: H Colorless solid; Yield 96%; M.p o C; IR (neat): 3410, 3048, 1451, 1319, 743 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 2H), (m, 3H), (m, 2H), 7.32 (d, 1H, J = 6.8 Hz), 7.38 (d, 1H, J = 8.0 Hz), 7.55 (d, 1H, J = 7.8 Hz) 8.19 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 19.8, 29.7, 111.2, 112.8, 118.9, 119.9, 120.0, 122.5, 126.8, 126.9, 127.6, 128.6, 129.0, 133.2, 136.7, 137.1; HRMS calcd. for C 16 H 14 1 (M + +1) , found a. 4a-Methyl-2,3,4,4a-tetrahydro-1H-carbazole: H 3 C Pale yellow oil; Yield 99%; IR (neat): 1582, 1444, 1190 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.16 (td, 1H, J = 13.2, 4.0 Hz), 1.30 (s, 3H), (m, 1H), (m, 2H), (m, 2H), 2.58 (td, 1H, J = 13.2, 5.6 Hz), 2.86 (d, 1H, J = 13.2 Hz), 7.19 (t, 1H, J = 7.2 Hz), (m, 2H), 7.59 (d, 1H, J = 7.6 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 19.9, 21.5, 29.1, 29.8, 38.7, 53.9, 120.3, 121.4, 124.9, 127.6, 146.9, 154.3, 190.3; HRMS calcd. for C 13 H 16 1 (M + +1) , found b. Ethyl 3-(2,3,4,4a-tetrahydro-1H-carbazol-4a-yl)propanoate: S6
7 OEt O Colorless oil; Yield 94%; IR (neat): 2930, 1725, 1583, 1451, 1377, 1174, 738 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.15 (t, 3H, J = 7.2 Hz, COOCH 2 CH 3 ), (m, 1H), (m, 1H), (m, 2H), (m, 1H), (m, 1H), (m, 2H), (m, 2H), 2.55 (dt, 1H, J = 13.2, 5.6 Hz), (m, 1H), (m, 2H, COOCH 2 CH 3 ), (m, 1H), (m, 1H), (m, 1H), 7.59 (d, 1H, J = 7.6 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 14.1 (CH 3 ), 21.2, 28.6, 28.7, 29.1, 30.1, 38.3, 57.5, 60.5 (OCH 2 ), 120.4, 121.7, 125.1, 127.9, 143.9, 155.1, (C=O), (C=); HRMS calcd. for C 17 H 22 O 2 (M + +1): , found c. 4a-(2-Azidoethyl)-2,3,4,4a-tetrahydro-1H-carbazole: 3 Colorless liquid; Yield 92%; IR (neat): 2920, 2857, 2157, 2091, 1584, 1446, 1258, 758 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.18 (td, 1H, J = 13.6, 4.0 Hz), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 2H, CH 2 3 ), (m, 1H, =CCH 2 ), (m, 1H, =CCH 2 ), 7.22 (d, 1H, J = 7.2 Hz), 7.27 (d, 1H, J = 7.6 Hz), 7.35 (t, 1H, J = 7.2 Hz), 7.61 (d, 1H, J = 7.6 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 21.3, 29.2, 30.3, 33.2, 39.0, 47.1 (CH 2 3 ), 56.7, 120.6, 121.5, 125.2, 128.2, 143.5, 155.0, (C=); HRMS calcd. for C 14 H 17 4 (M + +H) , found d. 4a-Allyl-2,3,4,4a-tetrahydro-1H-carbazole: Pale yellow oil; Yield 90%; IR (neat): 2935, 1584, 1448, 920, 762 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.15 (td, 1H, J = 13.6, 4.0 Hz), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H) (m, 3H), (m, 1H), 4.85 (d, 1H, J = 10.0 Hz), 4.94 (d, 1H, J = 16.8 Hz), (m, 1H), (m, 1H), (m, 2H), 7.58 (d, 1H, J = 7.6 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 21.2, 29.0, 30.3,. 37.0, 37.8, 57.8, 118.1, 120.2, 122.0, 124.8, 127.7, 132.3, 144.7, 155.0, 189.0; HRMS calcd. for C 15 H 18 1 (M + +1) , found e. 3-(2,3,4,4a-Tetrahydro-1H-carbazol-4a-yl)propanenitrile: S7
8 C Pale yellow oil; Yield 90%; IR (neat): 1582, 1444, 1190 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.25 (td, 1H, J = 13.6, 4.8 Hz), (m, 1H), 1.59 (t, 2H, J = 8.4 Hz), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 1H), (m, 2H), (m, 1H), 7.62 (d, 1H, J = 7.6 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 12.1, 21.3, 29.1, 29.9, 30.3, 38.2, 57.4, 119.1, 120.9, 121.6, 125.7, 128.7, 142.4, 155.1, 187.3; HRMS calcd. for C 15 H 17 2 (M + +1) , found Chloro-2,3,4,9-tetrahydro-1H-carbazole: Cl Colorless solid; Yield 97%; M.p o C; IR (neat): 3404, 2356, 1686, 1440, 799 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), 2.66 (t, 2H, J = 6.0 Hz), 2.72 (t, 2H, J = 5.6 Hz), 7.05 (dd, 1H, J = 8.4, 1.6 Hz), 7.17 (d, 1H, J = 8.4 Hz), 7.41 (s, 1H), 7.70 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 20.9, 23.1, 23.2, 23.4, 110.2, 111.3, 117.5, 121.2, 124.9, 129.1, 134.1, 135.9; HRMS calcd. for C 12 H 13 Cl (M + +1) , found ,8-Dichloro-2,3,4,9-tetrahydro-1H-carbazole: Cl Cl Pale yellow solid; Yield 90%; M.p o C; IR (neat): 3437, 2928, 1571, 1465, 858 cm - 1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), (m, 2H), 2.70 (t, 2H, J = 5.6 Hz), 7.07 (s, 1H), 7.28 (s, 1H), 7.86 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 20.9, 23.0, 23.1, 23.3, 111.3, 116.1, 116.3, 120.3, 124.7, 129.8, 131.4, 136.6; HRMS calcd. for C 12 H 11 Cl 2 (M + ) , found Methyl-2,3,4,9-tetrahydro-1H-carbazole: Me Colorless solid; Yield 96%; M.p o C; IR (neat): 3391, 2922, 1457, 795 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), 2.43 (s, 3H), (m, 4H), 6.92 (dd, 1H, J = 8.4, 1.2 Hz), 7.15 (d, 1H, J = 8.0 Hz), 7.24 (s, 1H), 7.54 (br s, 1H); 13 C MR H H H S8
9 (100 MHz, CDCl 3 ): δ 21.1, 21.6, 23.3, 23.4, 23.5, 109.8, 110.1, 117.7, 122.5, 128.2, 128.4, 134.0, 134.4; HRMS calcd. for C 13 H 16 (M + +1) , found Methoxy-2,3,4,9-tetrahydro-1H-carbazole: MeO Colorless solid; Yield 95%; M.p o C; IR (neat): 3390, 2916, 1590, 1484, 1219, 1028 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ (m, 4H), (m, 4H), 3.88 (s, 3H), 6.79 (dd, 1H, J = 8.8, 2.0 Hz), 6.92 (d, 1H, J = 2.4 Hz), 7.16 (d, 1H, J = 8.4 Hz), 7.59 (s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 21.1, 23.3, 23.4, 23.5, 56.1, 100.4, 110.1, 110.6, 111.1, 128.3, 130.8, 135.2, 154.0; HRMS calcd. for C 13 H 16 O (M + +H) , found Tert-butyl 8-methoxy-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate: MeO H Colorless solid; Yield 88%; M.p o C (dec); IR (neat): 3304, 1674, 1426, 735 cm - 1 ; 1 H MR (500 MHz, CDCl 3 ): δ 1.53 (s, 9H), 2.79 (s, 2H), 3.81 (s, 2H), 3.86 (s, 3H), 4.62 (s, 2H), 6.81 (d, 1H, J = 8.0 Hz), 6.91 (s, 1H), 7.19 (d, 1H, J = 7.0 Hz), 8.09 (br s, 1H); 13 C MR (125 MHz, CDCl 3 ): δ 23.7, 28.6, 40.8, 41.6, 56.0, 80.0, 100.1, 107.3, 111.3, 111.5, 126.1, 131.1, 132.7, 133.3, 154.2, 155.4; HRMS calcd. for C 17 H 23 2 O 3 (M + +1) , found (5,7-Dichloro-1H-indol-3-yl)propan-1-ol: H O O Cl OH Cl H Pale yellow oil; Yield 90%; IR (neat): , 2932, 1564, 1039 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.95 (quin, 2H, J = 6.4 Hz, CH 2 -CH 2 -CH 2 ), 2.80 (t, 2H, J = 7.6 Hz), 3.71 (t, 2H, J = 6.4 Hz, CH 2 -OH), 7.07 (d, 1H, J = 2.0 Hz), 7.18 (d, 1H, J = 1.6 Hz), 7.48 (d, 1H, J = 1.6 Hz), 8.27 (br s, 1H, H); 13 C MR (100 MHz, CDCl 3 ): δ 21.4, 32.9, 62.4 (CH 2 -OH), 117.1, 117.2, 117.4, 121.6, 123.4, 125.0, 129.5, 132.3; HRMS calcd. for C 11 H 12 OCl 2 (M + +1) , found (5-Methoxy-1H-indol-3-yl)ethanol: S9
10 MeO OH Colorless oil; Yield 92%; IR (neat): , 1493, 1282, 1034, 826 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 3.0 (t, 2H, J = 6.4 Hz), 3.87 (s, 3H), 3.90 (t, 2H, J = 6.4 Hz), 6.87 (dd, 1H, J = 8.8, 2.4 Hz), 7.05 (d, 2H, J = 2.2 Hz), 7.25 (d, 1H, J = 8.8 Hz), 8.04 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 28.8, 56.1, 62.7, 100.7, 112.0, 112.1, 112.5, 123.4, 127.9, 131.7, 154.1; HRMS calcd. for C 11 H 14 O 2 (M + +H) , found A. 3-(2-Iodoethyl)-5-methoxy-1H-indole: H MeO I Colorless solid; Yield 97%; 1 H MR (400 MHz, CDCl 3 ): δ (m, 2H), (m, 2H), 3.86 (s, 3H), 6.85 (dd, 1H, J = 8.8, 2.4 Hz), 6.98 (d, 1H, J = 2.4 Hz), 7.04 (d, 1H, J = 2.0 Hz), 7.24 (d, 1H, J = 2.4 Hz), 7.99 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 6.3, 30.5, 56.1, 100.4, 112.2, 112.5, 115.4, 122.8, 127.3, 131.4, B. 3-(2-Azidoethyl)-5-methoxy-1H-indole: H MeO 3 Colorless oil; Yield 96%; 1 H MR (400 MHz, CDCl 3 ): δ 3.02 (t, 2H, J = 7.2 Hz), 3.55 (t, 2H, J = 7.2 Hz), 3.87 (s, 3H), 6.87 (dd, 1H, J = 8.8, 2.4 Hz), (m, 2H), 7.23 (d, 1H, J = 8.8 Hz), 7.96 (br s, 1H); 13 C MR (100 MHz, CDCl 3 ): δ 25.2, 51.7, 56.1, 100.5, 112.1, 112.5, 123.2, 127.6, 131.5, IV. -(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide: MeO H Colorless solid; Yield 95%; M.p o C; IR (neat): 3402, 1650, 1627, 1397, 1038 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 1.81 (s, 3H), 2.83 (t, 2H, J = 6.8 Hz), 3.47 (q, 2H, J = 6.4 Hz), 3.75 (s, 3H), 5.62 (br s, 1H), 6.76 (dd, 2H, J = 8.8, 2.4 Hz), 6.88 (d, 1H, J = 2.0 Hz), 6.93 (d, 1H, J = 2.4 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 23.4, 25.4, 39.9, 56.1, 100.6, 112.2, 112.4, 112.6, 123.0, 127.8, 131.7, 154.1, 170.4; HRMS calcd. for C 13 H 17 2 O 2 (M + +H) , found H H CH Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole: O S10
11 Me Me Colorless solid; Yield 91%; M.p o C; IR (neat): 3334, 2923, 1634, 1463, 795 cm -1 ; 1 H MR (400 MHz, CDCl 3 ): δ 2.43 (s, 3H), 2.58 (s, 3H), 2.85 (s, 4H), 3.69 (s, 2H), 6.94 (d, 1H, J = 8.4 Hz), 7.15 (s, 1H), 7.17 (d, 2H, J = 3.6 Hz); 13 C MR (100 MHz, CDCl 3 ): δ 21.6, 23.7, 45.7, 51.8, 52.5, 107.9, 110.4, 117.5, 122.8, 126.4, 128.6, 131.8, 134.5; HRMS calcd. for C 13 H 17 2 (M + +1) , found H S11
12 H Expanded 1 H MR spectra of compound 3a S12
13 S13 Expanded 1 H MR spectrum of indole derivative 3a
14 H 13 C MR spectrum of indole derivative 3a S14
15 H 1 H MR spectrum of indole derivative 3b S15
16 S16 Expanded 1 H MR spectrum of indole derivative 3b
17 H 13 C MR spectrum of indole derivative 3b S17
18 H 1 H MR spectrum of indole derivative 3c S18
19 S19 Expanded 1 H MR spectrum of indole derivative 3c
20 H 13 C MR spectrum of indole derivative 3c S20
21 H 1 H MR spectrum of indole derivative 3d S21
22 S22 Expanded 1 H MR spectrum of indole derivative 3d
23 H 13 C MR spectrum of indole derivative 3d S23
24 CH 3 H 3 C H 1 H MR spectrum of indole derivative 3e S24
25 S25 Expanded 1 H MR spectrum of indole derivative 3e
26 CH 3 H 3 C H 13 C MR spectrum of indole derivative 3e S26
27 Ph H 1 H MR spectrum of indole derivative 3f S27
28 S28 Expanded 1 H MR spectrum of indole derivative 3f
29 Ph H 13 C MR spectrum of indole derivative 3f S29
30 Current Data Parameters AME sb40712 EXPO 64 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVET CDCl3 S 32 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec TD0 1 ======== CHAEL f1 ======== UC1 1H P usec PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC lab sb sb-sg-1727 iitm_proto-1to20 CDCl3 /opt/topspin nmr 2 Boc H ppm H MR spectrum of indole derivative 3g S30
31 lab sb sb-sg-1727 iitm_proto-1to20 CDCl3 /opt/topspin nmr ppm ppm ppm Expanded 1 H MR spectrum of indole derivative 3g S31
32 Current Data Parameters AME sb40712 EXPO 70 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD SOLVET CDCl3 S 5606 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec D sec TD0 1 ======== CHAEL f1 ======== UC1 13C P usec PLW W SFO MHz ======== CHAEL f2 ======== CPDPRG2 waltz16 UC2 1H PCPD usec PLW W PLW W PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 3.00 Hz GB 0 PC Boc lab sb sb-sg-1727 iitm_carbonshort CDCl3 /opt/topspin nmr 1 H ppm 13 C MR spectrum of indole derivative 3g S32
33 Current Data Parameters AME sb40712 EXPO 72 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB- PULPROG deptsp135 TD SOLVET CDCl3 S 1335 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K CST D sec D sec D sec TD0 1 ======== CHAEL f1 ======== UC1 13C P usec P usec PLW0 0 W PLW W SFO MHz SPAM5 Crp60comp.4 SPOAL SPOFFS5 0 Hz SPW W ======== CHAEL f2 ======== CPDPRG2 waltz16 UC2 1H P usec P usec PCPD usec PLW W PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 3.00 Hz GB 0 PC Boc lab sb sb-sg-1727 iitm_c13dept135 CDCl3 /opt/topspin nmr 1 H ppm 13 C DEPT MR spectrum of indole derivative 3g S33
34 lab sb sb-sg-1727 COSYGPSW CDCl3 /opt/topspin nmr 1 ppm Current Data Parameters AME sb40712 EXPO 74 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB- PULPROG cosygpppqf TD 2048 SOLVET CDCl3 S 1 DS 8 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec D sec D sec D sec D sec D sec I sec ======== CHAEL f1 ======== UC1 1H P usec P usec P usec PLW W PLW W SFO MHz ====== GRADIET CHAEL ===== GPAM1 SMSQ GPZ % P usec F1 - Acquisition parameters TD 128 SFO MHz FIDRES Hz SW ppm FnMODE QF F2 - Processing parameters SI 1024 SF MHz WDW QSIE SSB 0 LB 0 Hz GB 0 PC 1.40 F1 - Processing parameters SI 1024 MC2 QF SF MHz WDW SSB 0 LB 0 Hz GB 0 Boc H ppm 11 H 1 H COSY MR spectrum of indole derivative 3g S34
35 O Ph O H 1 H MR spectrum of indole derivative 3h S35
36 S36 Expanded 1 H MR spectrum of indole derivative 3h
37 O O Ph H 13 C MR spectrum of indole derivative 3h S37
38 Ph O O H 13 C DEPT MR spectrum of indole derivative 3h S38
39 1 H 1 H COSY MR spectrum of indole derivative 3h O O Ph H S39
40 H 1 H MR spectrum of indole derivative 3i S40
41 S41 Expanded 1 H MR spectrum of indole derivative 3i
42 13 C MR spectrum of indole derivative 3i H S42
43 Ph H 3 C H 1 H MR spectrum of indole derivative 3j S43
44 S44 Expanded 1 H MR spectrum of indole derivative 3j
45 Ph H 3 C H 13 C MR spectrum of indole derivative 3j S45
46 H3 C H 3 C CH 3 H 1 H MR spectrum of indole derivative 3k S46
47 S47 Expanded 1 H MR spectrum of indole derivative 3k
48 H3 C H 3 C CH 3 H 13 C MR spectrum of indole derivative 3k S48
49 HO H 1 H MR spectrum of indole derivative 3l S49
50 S50 Expanded 1 H MR spectrum of indole derivative 3l
51 HO H 13 C MR spectrum of indole derivative 3l S51
52 OH H 1 H MR spectrum of indole derivative 3m S52
53 S53 1 H MR expansion spectrum of indole derivative 3m
54 OH H 13 C MR spectrum of indole derivative 3m S54
55 MeO 2 C CO 2 Me H 1 H MR spectrum of indole derivative 3n S55
56 S56 Expanded 1 H MR spectrum of indole derivative 3n
57 MeO 2 C CO 2 Me H 13 C MR spectrum of indole derivative 3n S57
58 MeO 2 C CO 2 Me H 13 C DEPT MR spectrum of indole derivative 3n S58
59 MeO 2 C CO 2 Me 1 H 1 H 1 H COSY MR MR spectrum spectra of indole compound derivative 3n 3n H S59
60 H 1 H MR spectrum of indole derivative 3o S60
61 S61 Expanded 1 H MR spectrum of indole derivative 3o
62 H 13 C MR spectrum of indole derivative 3o S62
63 H 3 C 1 H MR spectrum of indolenine derivative 5a S63
64 S64 Expanded 1 H MR spectrum of indolenine derivative 5a
65 H 3 C 13 C MR spectrum of indolenine derivative 5a S65
66 EtOOC 1 H MR spectrum of indolenine derivative 5b S66
67 S67 Expanded 1 H MR spectrum of indolenine derivative 5b
68 S68 Expanded 1 H MR spectrum of indolenine derivative 5b
69 EtOOC 13 C MR spectrum of indolenine derivative 5b S69
70 EtOOC 13 C DEPT MR spectrum of indolenine derivative 5b S70
71 EtOOC 1 H 1 H COSY MR spectrum of indolenine derivative 5b S71
72 3 1 H MR spectrum of indolenine derivative 5c S72
73 S73 Expanded 1 H MR spectrum of indolenine derivative 5c
74 S74 Expanded 1 H MR spectrum of indolenine derivative 5c
75 3 13 C MR spectrum of indolenine derivative 5c S75
76 13 C DEPT MR spectrum of indolenine derivative 5c 3 S76
77 3 1 H 1 H COSY MR spectrum of indolenine derivative 5c S77
78 1 H MR spectrum of indolenine derivative 5d S78
79 S79 Expanded 1 H MR spectrum of indolenine derivative 5d
80 S80 Expanded 1 H MR spectrum of indolenine derivative 5d
81 13 C MR spectrum of indolenine derivative 5d S81
82 13 C DEPT MR spectrum of indolenine derivative 5d S82
83 1 H 1 H COSY MR spectrum of indolenine derivative 5d S83
84 C 1 H MR spectrum of indolenine derivative 5e S84
85 S85 Expanded 1 H MR spectrum of indolenine derivative 5e
86 S86 Expanded 1 H MR spectrum of indolenine derivative 5e
87 C 13 C MR spectrum of indolenine derivative 5e S87
88 13 C DEPT MR spectrum of indolenine derivative 5e C S88
89 C 1 H 1 H COSY MR spectrum of indolenine derivative 5e S89
90 H Cl 1 H MR spectrum of indole derivative 10 S90
91 S91 Expanded 1 H MR spectrum of indole derivative 10
92 Cl H 13 C MR spectrum of indole derivative 10 S92
93 1 H MR spectrum of indole derivative 11 H Cl Cl S93
94 S94 Expanded 1 H MR spectrum of indole derivative 11
95 13 C MR spectrum of indole derivative 11 H Cl Cl S95
96 H 1 H MR spectrum of indole derivative 12 Me S96
97 S97 Expanded 1 H MR spectrum of indole derivative 12
98 Me H 13 C MR spectrum of indole derivative 12 S98
99 Current Data Parameters AME sb40612 EXPO 171 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVET CDCl3 S 16 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec TD0 1 ======== CHAEL f1 ======== UC1 1H P usec PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC MeO sb-sg-1007 iitm_proto-5to15 CDCl3 /opt/topspin nmr 9 H ppm H MR spectrum of indole derivative 13 S99
100 lab sb sb-sg-1007 iitm_proto-5to15 CDCl3 /opt/topspin nmr ppm ppm ppm Expanded 1 H MR spectrum of indole derivative 13 S100
101 Current Data Parameters AME sb40612 EXPO 172 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB- PULPROG zgpg30 TD SOLVET CDCl3 S 1000 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec D sec TD0 1 ======== CHAEL f1 ======== UC1 13C P usec PLW W SFO MHz ======== CHAEL f2 ======== CPDPRG2 waltz16 UC2 1H PCPD usec PLW W PLW W PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 1.00 Hz GB 0 PC MeO H sb-sg-1007 iitm_carbonshort CDCl3 /opt/topspin nmr ppm 13 C MR spectrum of indole derivative 13 S101
102 Current Data Parameters AME sb50712 EXPO 42 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zg30 TD SOLVET CDCl3 S 32 DS 2 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec TD0 1 ======== CHAEL f1 ======== UC1 1H P usec PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC Boc MeO ppm Lab SB sb/sg/1728 iitm_proto CDCl3 /opt/topspin iitm 15 H H MR spectrum of indole derivative 14 S102
103 Lab SB sb/sg/1728 iitm_proto CDCl3 /opt/topspin iitm ppm ppm ppm Expanded 1 H MR spectrum of indole derivative 14 S103
104 Current Data Parameters AME sb50712 EXPO 51 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB/ PULPROG zgpg30 TD SOLVET CDCl3 S DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec D sec TD0 1 ======== CHAEL f1 ======== UC1 13C P usec PLW W SFO MHz ======== CHAEL f2 ======== CPDPRG2 waltz16 UC2 1H PCPD usec PLW W PLW W PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 3.00 Hz GB 0 PC Boc MeO Lab SB sb-sg-1728 iitm_carbonshort CDCl3 /opt/topspin iitm 2 H ppm 13 C MR spectra of compound 14 S104
105 Current Data Parameters AME sb50712 EXPO 44 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB/ PULPROG deptsp135 TD SOLVET CDCl3 S 1000 DS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K CST D sec D sec D sec TD ppm ======== CHAEL f1 ======== UC1 13C P usec P usec PLW0 0 W PLW W SFO MHz SPAM5 Crp60comp.4 SPOAL SPOFFS5 0 Hz SPW W ======== CHAEL f2 ======== CPDPRG2 waltz16 UC2 1H P usec P usec PCPD usec PLW W PLW W SFO MHz F2 - Processing parameters SI SF MHz WDW EM SSB 0 LB 3.00 Hz GB 0 PC Boc MeO H Lab SB sb/sg/1728 iitm_c13dept135 CDCl3 /opt/topspin iitm C DEPT MR spectrum of indole derivative 14 S105
106 Lab SB sb-sg-1728 COSYGPSW CDCl3 /opt/topspin iitm 2 ppm Current Data Parameters AME sb50712 EXPO 50 PROCO 1 F2 - Acquisition Parameters Date_ Time ISTRUM spect PROBHD 5 mm PABBO BB/ PULPROG cosygpppqf TD 2048 SOLVET CDCl3 S 1 DS 8 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec TE K D sec D sec D sec D sec D sec D sec I sec ======== CHAEL f1 ======== UC1 1H P usec P usec P usec PLW W PLW W SFO MHz ====== GRADIET CHAEL ===== GPAM1 SMSQ GPZ % P usec F1 - Acquisition parameters TD 128 SFO MHz FIDRES Hz SW ppm FnMODE QF F2 - Processing parameters SI 1024 SF MHz WDW QSIE SSB 0 LB 0 Hz GB 0 PC 1.40 F1 - Processing parameters SI 1024 MC2 QF SF MHz WDW SSB 0 LB 0 Hz GB 0 Boc MeO H ppm 1 H 1 H COSY MR spectrum of indole derivative 14 S106
107 OH H Cl Cl 1 H MR spectrum of indole derivative 15 S107
108 S108 Expanded 1 H MR spectrum of indole derivative 15
109 OH H Cl Cl 13 C MR spectrum of indole derivative 15 S109
110 OH H 1 H MR spectrum of indole derivative 16 MeO S110
111 S111 Expanded 1 H MR spectrum of indole derivative 16
112 OH H MeO 13 C MR spectrum of indole derivative 16 S112
113 I MeO H 1 H MR spectrum of indole derivative 16A S113
114 S114 Expanded 1 H MR spectrum of indole derivative 16A
115 I H MeO 13 C MR spectrum of indole derivative 16A S115
116 3 MeO H 1 H MR spectrum of indole derivative 16B S116
117 S117 Expanded 1 H MR spectrum of indole derivative 16B
118 3 H MeO 13 C MR spectrum of indole derivative 16B S118
119 H 3 C O 1 H MR spectrum of indole derivative IV H H MeO S119
120 S120 Expanded 1 H MR spectrum of indole derivative IV
121 H 3 C H O H 13 C MR spectrum of indole derivative IV MeO S121
122 13 C DEPT MR spectrum of indole derivative IV H 3 C O H H MeO S122
123 H 3 C O H MeO H 1 H 1 H COSY MR spectrum of indole derivative IV S123
124 Me Me H 1 H MR spectrum of indole derivative 17 S124
125 S125 Expanded 1 H MR spectrum of indole derivative 17
126 Me H Me 13 C MR spectrum of indole derivative 17 S126
127 Me Me H 13 C DEPT MR spectrum of indole derivative 17 S127
128 Me H 1 H 1 H COSY MR spectrum of indole derivative 17 Me S128
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