Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles
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1 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut für Katalyse e.v. an der Universität Rostock, Albert-Einstein-Str. 29a, D Rostock, Germany. Fax: ; Tel: ; matthias.beller@catalysis.de General Information All reactions were carried out under argon atmosphere. Reactions were monitored by TLC analysis (pre-coated silica gel plates with fluorescent indicator UV 254, 0.2 mm) and visualized with 254 nm UV light or iodine. Chemicals were purchased from Aldrich, Fluka, Acros, AlfaAsar, Strem and unless otherwise noted were used without further purification. All compounds were characterized by 1 MR, 13 C MR, GC-MS, RMS and IR spectroscopy. 1 spectra were recorded on Bruker AV 300 and AV 400 spectrometers. 13 C MR and 19 F MR spectra were recorded at 75.5 Mz and 282 Mz respectively. Chemical shifts are reported only for major rotamer (short signals on MR scans belong to minor rotamer) in ppm relative to the center of solvent resonance. lting points were determined on a digital SMP3 (Stuart). IR spectra were recorded on FT-IR ALPA (Bruker) with Platinum-ATR (Bruker). EI (70 ev) mass spectra were recorded on MAT 95XP (Thermo ELECTR CRPRATI). GC was performed on Agilent 6890 chromatograph with a 30 m P5 column. RMS was performed on MAT 95XP (EI) and Agilent 6210 Time-of-Flight LC/MS (ESI). GC-MS was performed on Agilent 5973 chromatograph Mass Selective Detector. All yields reported refer to isolated yields. General procedure: a) Conventioanl heating: In an Ace-pressure tube to a solution of alkyne derivative 2a c (1 mmol) and arylhydrazine derivative 1a h (1.5 mmol) in 1,2-dimethoxyethane or toluene (3 ml), zinc bromide or zinc chloride (3 mmol) was added under argon atmosphere. The pressure tube was fitted with a Teflon cap and heated at 110 C for 20 h (TLC control). After removal of the solvent, the crude product 5 12 was purified by column chromatography and recrystallized using heptane with ethyl acetate, acetone or dichloromethane. b) Microwave irradiation: A mixture of hydrazine 1 (1.5 mmol), propargylamide 2d l (1.0 mmol) and zinc bromide (1 3 mmol) in 1,2-dimethoxyethane (2 ml) was heated in reaction vial in CEM Discover microwave reactor cavity for 1 h at C. After removal of the solvent, the corresponding crude product was purified by column chromatography using heptane/ethyl acetate. -(2-thyl-5-(trifluoromethyl)-1-indol-3-yl)acetamide (5) F 3 C Ac Yield: 182 mg (71%); white crystals; Mp 224 C (from acetone/heptane); R f = 0.55 (solvent ethyl acetate/ethanol 20:1); 1 MR (300 Mz, Acetone-d 6 ): δ = 2.15 (s, 3), 2.29 (s, 3), 7.28 (dd, 1, J ~ 1.6, 8.5 z), 7.38 (d, 1, J ~ 8.5 z), 7.72 (s, 1), 8.66 (s, 1), (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.2, 22.7, 111.6, 112.3, (q, J = 4.5 z), (q, J ~ 3.5 z), (q, J = 31.3 z), 125.3, (q, J = z), 132.8, 136.1, 169.2; GC-MS (EI, 70 ev): m/z (%) 256 (52) [M + ]; RMS (EI): Calc for C F 3 : ; found: 1
2 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry ; FTIR (ATR, cm -1 ): 3248, 3064, 2993, 2967, 2928, 2838, 2712, 1631, 1548, 1329, 1279, 1243, 1155, 1111, 1048, 1013, 893, 812, 697, 682, 657, 624, 599, 564, 535, (2,5-Dimethyl-1-indol-3-yl)acetamide (6) Ac Yield: 121 mg (60%); yellow crystals; Mp 208 C (from acetone/heptane); R f = 0.47 (solvent ethyl acetate/ethanol 20:1); 1 MR (300 Mz, DMS-d 6 ): δ = 2.03 (s, 3), 2.19 (s, 3), 2.33 (s, 3), 6.81 (dd, 1, J = 1.5, 8.1 z), 7.04 (s, 1), 7.11 (d, 1, J = 8.2 z), 9.11 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.3, 21.3, 22.7, 109.9, 110.3, 117.0, 121.7, 125.2, 126.6, 129.6, 132.0, 168.5; GC-MS (EI, 70 ev): m/z (%) 202 (55) [M + ]; RMS (EI): Calc for C : ; found: ; FTIR (ATR, cm -1 ): 3230, 3208, 3066, 3026, 2976, 2917, 2860, 2781, 1623, 1549, 1461, 1424, 1369, 1315, 1294, 1247, 1133, 1023, 800, 794, 772, 753, 696, (5-thoxy-2-methyl-1-indol-3-yl)acetamide (8) Ac Yield: 105 mg (48%); white crystals; Mp 159 C (from acetone/heptane); R f = 0.5 (solvent ethyl acetate/ethanol 10:1); 1 MR (300 Mz, Acetone-d 6 ): δ = 2.11 (s, 3), 2.21 (s, 3), 3.73 (s, 3), 6.64 (dd, 1, J = 2.4, 8.7 z), 6.86 (d, 1, J = 2.5 z), 7.09 (d, 1, J = 8.7 z), 8.52 (s, 1), 9.84 (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.3, 22.7, 55.4, 99.8, 110.8, 111.2, 111.7, 126.4, 129.7, 131.2, 154.3, 169.1; GC-MS (EI, 70 ev): m/z (%) 218 (77) [M + ]; RMS (EI): Calc for C : ; found: ; FTIR (ATR, cm -1 ): 3239, 3073, 2999, 2976, 2954, 2910, 2831, 1623, 1546, 1487, 1471, 1453, 1423, 1369, 1293, 1244, 1218, 1138, 1110, 1035, 839, 811, 767, 746, 691, (1-Benzyl-2-methyl-1-indol-3-yl)acetamide (9) Ac Yield: 128 mg (46%); white crystals; Mp 178 C (from acetone/heptane); R f = 0.34 (solvent ethyl acetate/heptane 2:1); 1 MR (300 Mz, DMS-d 6 ): δ = 2.06 (s, 3), 2.19 (s, 3), 5.39 (s, 2), 7.01 (m, 4), 7.27 (m, 4), 7.38 (d, 1, Bn J = 7.7 z), 9.26 (s, 1); 13 C MR (DMS-d 6 ): δ = 10.0, 22.7, 45.8, 109.5, 110.9, 117.7, 118.8, 120.7, 124.3, (2C), 127.1, (2C), 131.0, 134.5, 138.4, 168.6; MS (EI): m/z (%) 278 (100) [M + ]; RMS pos. (ESI): Calc for [M+] +, C : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a: ; found: ; FTIR (ATR, cm -1 ): 3276, 3189, 3054, 3032, 2933, 2911, 1643, 1597, 1513, 1499, 1468, 1373, 1350, 1338, 1033, 732, 723, 698, (1-Benzyl-2-methyl-1-indol-3-yl)benzamide (10) Bz Yield: 300 mg (88%); white crystals; Mp from 169 C (from acetone/heptane); R f = 0.47 (solvent ethyl acetate/heptane 1:1); 1 MR (300 Mz, CDCl 3 ): δ = 2.27 (s, 3), 5.26 (s, 2), 7.03 (m, 2), 7.14 (m, 2), 7.26 (m, 4), 7.47 (m, Bn 3), 7.55 (m, 1), 7.76 (s, 1), 7.96 (m, 2); 13 C MR (CDCl 3 ): δ = 10.2, 46.6, 109.3, 109.8, 117.3, 119.8, 121.4, 124.5, (2C), (2C), , (2C), (2C), 131.6, 132.2, 134.5, 135.1, 137.5, 166.8; GC-MS (EI): m/z (%) 340 (88) [M + ]; RMS (EI): Calc for C : ; found: ; FTIR (ATR, cm -1 ): 3273, 3059, 3030, 2914, 1643, 1515, 1468, 1452, 1372, 1353, 1339, 1283, 1199, 1028, 736, 708, (1,2-Dimethyl-1-indol-3-yl)benzamide (11) 2
3 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry Bz Yield: 161 mg (61%); white crystals; Mp 199 C (from acetone/heptane); R f = 0.49 (solvent ethyl acetate/heptane 2:1); 1 MR (400 Mz, CDCl 3 ): δ = 2.34 (s, 3), 3.65 (s, 3), 7.09 (m, 1), 7.18 (ddd, 1, J ~ 1.1, 7.0, 8.2 z), 7.28 (d, 1, J = 8.2 z), 7.28 (d, 1, J = 7.8 z), 7.48 (m, 2), 7.56 (m, 2), 7.95 (m, 2); 13 C MR (CDCl 3 ): δ = 10.2, 29.6, , , 117.0, 119.5, 121.1, 124.3, (2C), (2C), 131.6, 132.5, 134.6, 135.2, 166.9; GC-MS (EI): m/z (%) 264 (50) [M + ]; RMS (EI): Calc for C : ; found: ; FTIR (ATR, cm -1 ): 3190, 3064, 3039, 2982, 2939, 2908, 2851, 1627, 1579, 1510, 1477, 1447, 1372, 1336, 1304, 1289, 1252, 1195, 919, 813, 743, 717, 696, (1-Benzyl-2-methyl-1-indol-3-yl)isoindoline-1,3-dione (12) Bn Yield: 201 mg (55%); yellow crystals; Mp 229 C (from acetone/heptane); R f = 0.38 (solvent ethyl acetate/heptane 1:2); 1 MR (300 Mz, CDCl 3 ): δ = 2.29 (s, 3), 5.38 (s, 2), 7.14 (m, 4), 7.31 (m, 5), 7.81 (ddd, 2, J ~ 1.2, 5.1, 10.6 z), 7.99 (m, 2); 13 C MR (CDCl 3 ): δ = 10.5, 46.9, 104.6, 109.7, 117.4, 120.4, 121.8, (2C), 124.3, (2C), 127.4, (2C), (2C), (3C), 135.5, 137.0, (2C); GC-MS (EI, 70 ev): m/z (%) 366 (100) [M + ]; RMS (EI): Calc for C : ; found: ; FTIR (ATR, cm -1 ): 3088, 3061, 3034, 3004, 2921, 1720, 1708, 1465, 1454, 1442, 1388, 1356, 1344, 1308, 1109, 1083, 878, 749, 717, 691, (5-bromo-2-methyl-1-indol-3-yl)-2-phenylacetamide (13) Br Yield: 206 mg (60%); white crystals; Mp 217 C (from acetone/heptane); R f = 0.46 (solvent ethyl acetate/heptane 2:1); 1 MR (300 Mz, DMS-d 6 ): δ = 2.20 (s, 3), 3.65 (s, 2), 7.09 (dd, 1, J = 2.0, 8.5 z), 7.20 (d, 1, J = 8.5 z), 7.25 (m, 1), 7.36 (m, 5), 9.48 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.2, 42.4, 109.8, 111.0, 112.7, 119.6, 122.6, 126.5, (2C), (2C), 131.4, 132.2, 136.7, 169.6; GC-MS (EI, 70 ev): m/z (%) 342 (70) [M + ], 344 (69) [M + ]; RMS pos. (ESI): Calc for [M+] +, C Br 2 : and ; found: and ; RMS pos. (ESI): Calc for [M+a] +, C Br 2 a: and ; found: and ; FTIR (ATR, cm -1 ): 3424, 3251, 3057, 3027, 2912, 1652, 1535, 1468, 1425, 1409, 1343, 1277, 1242, 1199, 979, 862, 800, 756, 734, 703, 649, 584, 576, 555, 524, 473, 420, (5-Bromo-2-methyl-1-indol-3-yl)cyclohexanecarboxamide (14) Br Yield: 216 mg (64%); white crystals; Mp 241 C (from acetone/heptane); R f = 0.54 (solvent ethyl acetate/heptane 2:1); 1 MR (400 Mz, DMS-d 6 ): δ = 1.26 (m, 3), 1.45 (m, 2), 1.65 (m, 1), 1.81 (m, 4), 2.20 (s, 3), 2.37 (tt, 1, J = 3.5, 11.5 z), 7.08 (dd, 1, J = 2.0, 8.5 z), 7.19 (d, 1, J = 8.5 z), 7.32 (d, 1, J = 1.8 z), 9.04 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.2, 25.4 (2C), 25.5, 29.6 (2C), 44.0, 109.9, 111.0, 112.6, 119.6, 122.5, 126.6, 131.3, 132.2, 174.8; GC-MS (EI, 70 ev): m/z (%) 334 (33.4) [M + ], 336 (34) [M + ]; RMS pos. (ESI): Calc for [M+] +, C Br 2 : and ; found: and ; RMS pos. (ESI): Calc for [M+a] +, C Br 2 a: and ; found: and ; FTIR 3
4 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry (ATR, cm -1 ): 3377, 3174, 2928, 2851, 1665, 1489, 1474, 1450, 1430, 1315, 1295, 1262, 1248, 1196, 1044, 861, 795, 757, 644, 625, 560, 515, 431, (5-Bromo-2-methyl-1-indol-3-yl)thiophene-2-carboxamide (15) Br S Yield: 198 mg (59%); light yellow crystals; Mp 239 C (dec.) (from acetone/heptane); R f = 0.43 (solvent ethyl acetate/heptane 1:1); 1 MR (400 Mz, DMS-d 6 ): δ = 2.29 (s, 3), 7.13 (dd, 1, J = 1.8, 8.5 z), 7.22 (dd, 1, J = 4.0, 4.6 z), 7.25 (d, 1, J = 8.5 z), 7.43 (d, 1, J = 1.4 z), 7.81 (d, 1, J = 4.9 z), 8.02 (dd, 1, J 0.5, 3.2 z), 9.82 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.4, 109.3, 111.2, 112.8, 119.7, 122.8, 126.6, 128.1, 128.8, 131.2, 132.2, 132.3, 139.9, 160.3; GC-MS (EI, 70 ev): m/z (%) 334 (90) [M + ], 336 (93) [M + ]; RMS pos. (ESI): Calc for [M+] +, C Br 2 S: and ; found: and ; RMS pos. (ESI): Calc for [M+a] +, C Br 2 as: and ; found: and ; FTIR (ATR, cm -1 ): 3329, 3098, 3075, 2920, 1649, 1597, 1514, 1467, 1447, 1336, 1287, 1207, 970, 867, 791, 762, 732, 718, 690, 644, 597, 542, 492, 450, (2-thyl-1-indol-3-yl)thiophene-2-carboxamide (16) S Yield: 154 mg (60%); light yellow crystals; Mp 221 C (dec.) (from acetone/heptane); R f = 0.55 (solvent ethyl acetate/heptane 3:1); 1 MR (400 Mz, Acetone-d 6 ): δ = 2.33 (s, 3), 6.96 (m, 1), 7.02 (m, 1), 7.18 (dd, 1, J = 3.8, 5.0 z), 7.26 (d, 1, J = 8.0 z), 7.39 (d, 1, J = 7.8 z), 7.71 (dd, 1, J = 0.8, 5.0 z), 7.97 (dd, 1, J = 0.7, 3.7 z), 9.06 (s, 1), (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.3, 110.6, 111.2, 117.9, 119.3, 121.2, 126.2, 128.3, 128.5, 130.9, 131.1, 134.8, 141.1, 161.0; GC-MS (EI, 70 ev): m/z (%) 256 (63) [M + ]; RMS pos. (ESI): Calc for [M+] +, C S: ; found: ; RMS pos. (ESI): Calc for [M+a] +, C as: ; found: ; FTIR (ATR, cm -1 ): 3339, 3069, 2922, 1615, 1525, 1506, 1285, 1243, 739, 709, 666, 648, 603, 555, 538, thyl--(2-methyl-1-indol-3-yl)thiophene-2-carboxamide (17) S Yield: 160 mg (59%); white crystals; Mp 246 C (dec.) (from ethyl acetate/heptane); R f = 0.59 (solvent ethyl acetate/heptane 3:1); 1 MR (400 Mz, DMS-d 6 ): δ = 2.27 (s, 6), 6.94 (ddd, 1, J 1.0, 7.1, 8.1 z), 7.02 (ddd, 1, J 1.3, 7.1, 8.1 z), 7.28 (m, 2), 7.38 (t, 1, J = 1.1 z), 7.85 (d, 1, J = 1.5 z), 9.70 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.4, 15.5, 109.6, 110.7, 117.4, 118.5, 120.3, 125.1, 126.3, 130.3, 130.5, 133.7, 137.9, 139.8, 160.4; GC-MS (EI, 70 ev): m/z (%) 270 (78) [M + ]; RMS pos. (ESI): Calc for [M+] +, C S: ; found: ; RMS pos. (ESI): Calc for [M+a] +, C as: ; found: ; FTIR (ATR, cm -1 ): 3333, 3063, 2916, 1615, 1550, 1516, 1459, 1422, 1285, 1243, 1221, 879, 866, 764, 738, 726, 651, 605, 588, 563, 543, 441, 426, thyl--(2-methyl-1-indol-3-yl)-1-pyrrole-2-carboxamide (18) Yield: 167 mg (66%); white crystals; Mp 230 C (dec.) (from acetone/heptane); R f = 0.58 (solvent ethyl acetate/heptane 3:1); 1 MR (400 Mz, Acetone-d 6 ): δ = 2.31 (s, 3), 3.94 (s, 3), 6.09 (t, 1, J = 3.2 4
5 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry z), 6.88 (t, 1, J = 2.1 z), 6.95 (ddd, 1, J 1.2, 7.2, 8.9 z), 7.00 (ddd, 1, J 1.4, 7.3, 9.3 z), 7.05 (br, 1), 7.24 (ddd, 1, J 1.0, 1.7, 7.8 z), 7.38 (m, 1), 8.57 (s, 1), 9.95 (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.3, 36.4, 107.4, 111.0, 111.1, 112.9, 118.0, 119.2, 121.0, 126.5, 126.7, 128.2, 130.9, 134.8, 161.2; GC-MS (EI, 70 ev): m/z (%) 253 (93) [M + ]; RMS pos. (ESI): Calc for [M+] +, C : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a: ; found: ; FTIR (ATR, cm -1 ): 3353, 3205, 2916, 1634, 1531, 1460, 1316, 1247, 1059, 733, 694, 657, 618, 593, 550, 533, 489, 473, 436, (2-thyl-1-indol-3-yl)-1-pyrrole-2-carboxamide (19) Yield: 110 mg (46%); white crystals; Mp 201 C (from acetone/heptane); R f = 0.46 (solvent ethyl acetate/heptane 3:1); 1 MR (400 Mz, Acetoned 6 ): δ = 2.30 (s, 3), 6.21 (br, 1), 6.95 (m, 2), 7.01 (m, 1), 7.06 (br, 1), 7.24 (d, 1, J = 7.8 z), 7.38 (d, 1, J = 7.8 z), 8.73 (s, 1), 9.97 (s, 1), (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.3, 109.6, 110.4, 110.7, 111.1, 117.9, 119.2, 121.0, 122.0, 126.3, 127.2, 130.9, 134.8, 160.6; GC-MS (EI, 70 ev): m/z (%) 239 (36) [M + ]; RMS pos. (ESI): Calc for [M+a] +, C a: ; found: ; FTIR (ATR, cm -1 ): 3398, 3259, 3034, 1623, 1594, 1569, 1519, 1331, 1311, 1245, 1137, 741, 637, 598, 583, 539, 478, 442, 428, thyl--(2-methyl-1-indol-3-yl)-1-indole-2-carboxamide (20) Yield: 191 mg (63%); white crystals; Mp 264 C (dec.) (from acetone/heptane); R f = 0.61 (solvent ethyl acetate/heptane 3:1); 1 MR (300 Mz, Acetone-d 6 ): δ = 2.39 (s, 3), 4.10 (s, 3), 6.98 (ddd, 1, J 1.4, 7.1, 8.9 z), 7.04 (ddd, 1, J 1.3, 7.1, 8.4 z), 7.13 (m, 1), 7.31 (m, 2), 7.37 (s, 1), 7.45 (br d, 1, J 7.5 z), 7.52 (dd, 1, J 0.6, 8.4 z), 7.67 (d, 1, J 8.0 z), 9.07 (s, 1), (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.4, 31.4, 105.0, 110.7, , , 118.1, 119.3, 120.7, 121.2, 122.2, 124.2, 126.2, 126.9, 130.9, 133.2, 134.8, 139.6, 161.7; GC-MS (EI, 70 ev): m/z (%) 303 (100) [M + ]; RMS pos. (ESI): Calc for [M+] +, C : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a: ; found: ; FTIR (ATR, cm -1 ): 3365, 3231, 1655, 1514, 1458, 1245, 1226, 747, 730, 682, 658, 604, 576, 538, 508, 433, thyl--(2-methyl-1-indol-3-yl)furan-2-carboxamide (21) Yield: 130 mg (51%); white crystals; Mp 225 C (from acetone/heptane); R f = 0.51 (solvent ethyl acetate/heptane 3:1); 1 MR (400 Mz, DMSd 6 ): δ = 2.25 (s, 3), 2.37 (s, 3), 6.29 (dd, 1, J = 0.8, 3.2 z), 6.93 (ddd, 1, J 1.0, 7.1, 8.1 z), 7.01 (ddd, 1, J 1.0, 7.1, 8.1 z), 7.18 (d, 1, J = 3.3 z), 7.27 (m, 2), 9.51 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.3, 13.6, 108.2, 109.3, 110.7, 114.9, 117.4, 118.4, 120.3, 125.2, 130.4, 133.7, 146.5, 154.5, 157.1; GC-MS (EI, 70 ev): m/z (%) 254 (74) [M + ]; RMS pos. (ESI): Calc for [M+a] +, C a 2 : ; found: ; FTIR (ATR, cm -1 ): 3381, 3238, 3130, 3053, 1651, 1546, 1504, 1430, 1284, 1021, 808, 745, 706, 661, 594, 562, 536,
6 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2-thyl-1-indol-3-yl)morpholine-4-carboxamide (22) Yield: 150 mg (58%); white crystals; Mp 240 C (dec.) (from acetone/heptane); R f = 0.55 (solvent ethyl acetate/ethanol 9:1); 1 MR (300 Mz, Acetone-d 6 ): δ = 2.25 (s, 3), 3.48 (m, 4), 3.64 (m, 4), 6.92 (ddd, 1, J 1.3, 7.2, 8.8 z), 6.97 (ddd, 1, J 1.4, 7.2, 9.2 z), 7.21 (m, 1), 7.24 (s, 1), 7.32 (m, 1), 9.87 (s, 1); 13 C MR (Acetone-d 6 ): δ = 10.9, 45.2 (2C), 66.9 (2C), 111.0, 112.1, 117.8, 118.9, 120.8, 126.9, 130.9, 134.7, 157.5; RMS pos. (ESI): Calc for [M+] +, C : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 2 : ; found: ; FTIR (ATR, cm -1 ): 3398, 3311, 3061, 2966, 2899, 2856, 1650, 1632, 1498, 1450, 1339, 1246, 1199, 1112, 997, 738, 652, 601, 565, 544, 436, 410, (2-thyl-5-(methylsulfonyl)-1-indol-3-yl)thiophene-2-carboxamide (23) 2 S S Yield: 180 mg (54%); white crystals; Mp from 259 C (from acetone/heptane); R f = 0.43 (solvent ethyl acetate/heptane 9:1); 1 MR (300 Mz, DMS-d 6 ): δ = 2.33 (s, 3), 3.13 (s, 3), 7.24 (dd, 1, J = 3.7, 5.0 z), 7.50 (d, 1, J = 8.6 z), 7.56 (dd, 1, J = 1.8, 8.6 z), 7.84 (dd, 1, J = 1.0, 5.0 z), 7.91 (d, 1, J = 1.5 z), 8.05 (dd, 1, J = 1.0, 3.7 z), 9.99 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.6, 22.8, 44.6, 111.0, 111.5, 117.6, 118.8, 124.2, 128.1, 129.0, 131.0, 131.4, 133.4, 135.7, 139.7, 160.3; GC-MS (EI): m/z (%) 334 (100) [M + ]; RMS pos. (ESI): Calc for [M+] +, C S 2 : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 3 S 2 : ; found: ; FTIR (ATR, cm -1 ): 3351, 3196, 3093, 3000, 2933, 2917, 2854, 1619, 1592, 1533, 1313, 1283, 1160, 1134, 1114, 1058, 949, 782, 722, 710, 618, 561, 541, 499, thyl--(2-methyl-5-(methylsulfonyl)-1-indol-3-yl)-1-pyrrole-2-carboxamide (24) 2 S Yield: 172 mg (52%); light yellow crystals; Mp from 233 C (dec.) (from acetone/heptane); R f = 0.45 (solvent ethyl acetate/heptane 9:1); 1 MR (300 Mz, Acetone-d 6 ): δ = 2.39 (s, 3), 3.03 (s, 3), 3.95 (s, 3), 6.10 (dd, 1, J = 2.6, 4.0 z), 6.91 (br t, 1, J = 2.1 z), 7.07 (br d, 1, J = 2.4 z), 7.48 (dd, 1, J = 0.6, 8.6 z), 7.58 (dd, 1, J = 1.7, 8.5 z), 8.02 (br d, 1, J = 1.6 z), 8.82 (s, 1), (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.9, 36.9, 45.2, 107.8, 112.0, 112.0, 113.6, 119.0, 120.0, 126.2, 126.6, 128.9, 132.8, 134.4, 137.1, 161.5; GC-MS (EI): m/z (%) 331 (57) [M + ]; RMS pos. (ESI): Calc for [M+] +, C S 1 : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 3 S 1 : ; found: ; FTIR (ATR, cm -1 ): 3341, 3260, 3131, 2922, 1634, 1516, 1294, 1255, 1181, 1131, 1104, 1058, 952, 754, 738, 654, 609, 563, 543, 507, thyl--(2-methyl-5-(methylsulfonyl)-1-indol-3-yl)furan-2-carboxamide (25) 2 S Yield: 173 mg (52%); white crystals; Mp from 263 C (dec.) (from acetone/heptane); R f = 0.44 (solvent ethyl acetate/heptane 9:1); 1 MR (400 Mz, DMS-d 6 ): δ = 2.30 (s, 3), 2.39 (s, 3), 3.11 (s, 3), 6.32 (dd, 1, J = 0.9, 3.3 z), 7.20 (d, 1, J = 3.3 z), 7.48 (dd, 1, J = 0.6, 8.4 z), 7.55 (dd, 1, J = 1.5, 8.6 z), 7.88 (d, 1, J = 1.7), 9.75 (s, 1), (s, 1); 13 C MR (DMS-d 6 ): δ = 11.6, 6
7 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 13.6, 44.6, 108.4, 110.7, 111.4, 115.4, 117.7, 118.7, 124.3, 130.9, 133.4, 135.7, 146.2, 154.8, 156.9; GC-MS (EI): m/z (%) 332 (86) [M + ]; RMS pos. (ESI): Calc for [M+] +, C S 1 : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 4 S 1 : ; found: ; FTIR (ATR, cm -1 ): 3367, 3282, 3203, 2997, 2918, 1628, 1549, 1507, 1319, 1285, 1138, 1117, 1057, 1017, 953, 796, 785, 754, 684, 600, 567, 541, 490, 424, (5-Isopropyl-2-methyl-1-indol-3-yl)thiophene-2-carboxamide (26) () 2 C S Yield: 185 mg (62%); white crystals; Mp 211 C (dec.) (from acetone/heptane); R f = 0.39 (solvent ethyl acetate/heptane 1:1); 1 MR (400 Mz, Acetone-d 6 ): δ = 1.23 (d, 6, J = 6.9 z ), 2.32 (s, 3), 2.93 (m, 1), 6.94 (dd, 1, J = 1.6, 8.3 z), 7.19 (d, 1, J = 8.5 z), 7.19 (d, 1, J = 1.1 z), 7.24 (s, 1), 7.72 (dd, 1, J = 0.9, 5.0 z), 7.98 (dd, 1, J = 0.7, 3.6 z), 9.03 (s, 1), 9.92 (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.4, 24.8 (2C), 34.7, , , 114.8, 120.2, 126.3, 128.3, 128.5, 130.9, 131.2, 133.4, 139.8, 141.4, 160.9; GC-MS (EI): m/z (%) 298 (70) [M + ]; RMS pos. (ESI): Calc for [M+] +, C S 1 : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 1 S 1 : ; found: ; FTIR (ATR, cm -1 ): 3369, 3308, 2953, 2919, 2861, 1612, 1600, 1524, 1494, 1458, 1288, 1249, 807, 714, 627, 566, 533, (5-Isopropyl-2-methyl-1-indol-3-yl)-1-methyl-1-pyrrole-2-carboxamide (27) () 2 C Yield: 159 mg (54%); white crystals; Mp 225 C (dec.) (from acetone/heptane); R f = 0.34 (solvent ethyl acetate/heptane 1:1); 1 MR (400 Mz, Acetone-d 6 ): δ = 1.23 (d, 6, J = 6.9 z ), 2.30 (s, 3), 2.93 (m, 1), 3.94 (s, 3), 6.09 (br t, 1, J = 3.1 z), 6.88 (br t, 1, J = 2.0 z), 6.93 (dd, 1, J = 1.7, 8.3 z), 7.09 (br, 1), 7.16 (d, 1, J = 8.3 z), 7.23 (br, 1), 8.53 (s, 1), 9.83 (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.4, 24.8 (2C), 34.7, 36.4, 107.3, , , 112.8, 114.8, 120.0, 126.6, 128.8, 128.2, 131.1, 133.5, 139.6, 161.2; GC-MS (EI): m/z (%) 295 (100) [M + ]; RMS pos. (ESI): Calc for [M+] +, C : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 1 : ; found: ; FTIR (ATR, cm -1 ): 3357, 3245, 2957, 2923, 2867, 1639, 1532, 1499, 1452, 1407, 1319, 1251, 1099, 799, 739, 708, 672, 656, 607, 576, 542, (5-Isopropyl-2-methyl-1-indol-3-yl)-5-methylfuran-2-carboxamide (28) () 2 C Yield: 181 mg (61%); white crystals; Mp 228 C (dec.) (from acetone/heptane); R f = 0.46 (solvent ethyl acetate/heptane 3:1); 1 MR (300 Mz, Acetone-d 6 ): δ = 1.23 (d, 6, J = 6.9 z ), 2.30 (s, 3), 2.37 (s, 3), 2.93 (m, 1), 6.24 (dd, 1, J 0.9, 3.3 z), 6.94 (dd, 1, J = 1.7, 8.3 z), 7.06 (d, 1, J = 3.3 z), 7.18 (d, 1, J = 8.4 z), 7.23 (br, 1), 8.80 (s, 1), 9.92 (s, 1); 13 C MR (Acetone-d 6 ): δ = 11.4, 13.4, 24.8 (2C), 34.7, 108.7, 110.0, 111.0, 114.8, 115.2, 120.1, 126.3, 131.1, 133.4, 139.7, 147.9, 155.0, 157.5; GC-MS (EI): m/z (%) 296 (95) [M + ]; RMS pos. (ESI): Calc for [M+] +, C : ; found: ; RMS pos. (ESI): Calc for [M+a] +, C a 2 : ; found: ; FTIR (ATR, cm -1 ): 3358, 3253, 2951, 2920, 2887, 1643, 1604, 1544, 1477, 1456, 1287, 1271, 1209, 1023, 794, 752, 676, 631, 611, 563, 539,
8 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2-thyl-5-(trifluoromethyl)-1-indol-3-yl)acetamide (5) 1 MR F 3 C Ac ppm C MR F 3 C Ac ppm 8
9 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2,5-Dimethyl-1-indol-3-yl)acetamide (6) 1 MR Ac ppm C MR Ac ppm 9
10 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-thoxy-2-methyl-1-indol-3-yl)acetamide (8) 1 MR Ac ppm C MR Ac ppm 10
11 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(1-Benzyl-2-methyl-1-indol-3-yl)acetamide (9) 1 MR Ac Bn ppm C MR Ac Bn ppm 11
12 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(1-Benzyl-2-methyl-1-indol-3-yl)benzamide (10) 1 MR Bz Bn ppm C MR Bz Bn ppm 12
13 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(1,2-Dimethyl-1-indol-3-yl)benzamide (11) 1 MR Bz ppm C MR Bz ppm 13
14 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 2-(1-Benzyl-2-methyl-1-indol-3-yl)isoindoline-1,3-dione (12) 1 MR Bn ppm C MR Bn ppm 14
15 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry Mixture of 2-((1-benzyl-1-indol-2-yl)methyl)isoindoline-1,3-dione (12-1) and 2-((1- benzyl-1-indol-3-yl)methyl)isoindoline-1,3-dione (12-2) 1 MR Bn Bn ppm C MR Bn Bn ppm 15
16 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-bromo-2-methyl-1-indol-3-yl)-2-phenylacetamide (13) 1 MR Br ppm C MR Br ppm 16
17 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-Bromo-2-methyl-1-indol-3-yl)cyclohexanecarboxamide (14) 1 MR Br ppm C MR Br ppm 17
18 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-Bromo-2-methyl-1-indol-3-yl)thiophene-2-carboxamide (15) 1 MR S Br ppm C MR Br S ppm 18
19 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2-thyl-1-indol-3-yl)thiophene-2-carboxamide (16) 1 MR S ppm C MR S ppm 19
20 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 4-thyl--(2-methyl-1-indol-3-yl)thiophene-2-carboxamide (17) 1 MR S ppm C MR S ppm 20
21 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 1-thyl--(2-methyl-1-indol-3-yl)-1-pyrrole-2-carboxamide (18) 1 MR ppm C MR ppm 21
22 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2-thyl-1-indol-3-yl)-1-pyrrole-2-carboxamide (19) 1 MR ppm C MR ppm 22
23 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 1-thyl--(2-methyl-1-indol-3-yl)-1-indole-2-carboxamide (20) 1 MR ppm C MR ppm 23
24 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 5-thyl--(2-methyl-1-indol-3-yl)furan-2-carboxamide (21) 1 MR ppm C MR ppm 24
25 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2-thyl-1-indol-3-yl)morpholine-4-carboxamide (22) 1 MR ppm C MR ppm 25
26 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(2-thyl-5-(methylsulfonyl)-1-indol-3-yl)thiophene-2-carboxamide (23) 1 MR S 2 S ppm 13 C MR S S ppm 26
27 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 1-thyl--(2-methyl-5-(methylsulfonyl)-1-indol-3-yl)-1-pyrrole-2-carboxamide (24) 1 MR 2 S ppm C MR S ppm 27
28 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry 5-thyl--(2-methyl-5-(methylsulfonyl)-1-indol-3-yl)furan-2-carboxamide (25) 1 MR 2 S ppm C MR S ppm 28
29 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-Isopropyl-2-methyl-1-indol-3-yl)thiophene-2-carboxamide (26) 1 MR S () 2 C ppm C MR () 2 C S ppm 29
30 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-Isopropyl-2-methyl-1-indol-3-yl)-1-methyl-1-pyrrole-2-carboxamide (27) 1 MR () 2 C ppm C MR () 2 C ppm 30
31 Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry -(5-Isopropyl-2-methyl-1-indol-3-yl)-5-methylfuran-2-carboxamide (28) 1 MR () 2 C ppm C MR () 2 C ppm 31
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