Supporting Information
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- Εφθαλία Βλαστός
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1 S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento A.B.A.C., Università degli Studi della Tuscia, Via S. Camillo De Lellis, Viterbo, Italy b Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive Università degli Studi La Sapienza, P.le A. Moro 5, Rome, Italy Content General methods: S2 Typical Procedure for the Preparation of the 2-Iodohydroxytyrosol Derivative 2a: S2 Typical Procedure for the Preparation of 2-Bromohydroxytyrosol Derivative 2b: S2 Typical Procedure for the Preparation of 2-Chlorohydroxytyrosol Derivative 2c: S3 Typical Procedure for the Preparation of 2-Arylhydroxytyrosol Derivatives 3: S3 Analytical Data of 2-Arylhydroxytyrosol Derivatives 3: S3 Preparation of 6a: S5 Preparation of 7a: S5 Preparation of 8a: S5 NMR Spectra: S7
2 S2 lting points were determined with a Büchi B-545 apparatus and are uncorrected. All of the reagents and solvents are commercially available and were used as purchased, without further purification. 2-Halohydroxytyrosol derivatives 2a-c were prepared according to general halogenation procedures described in literature. 1 2-Halohydroxytyrosol and 2-arylhydroxytyrosol derivatives were purified on axially compressed columns, packed with Si µm (Macherey Nagel), connected to a Gilson solvent delivery system and to a Gilson refractive index detector, and eluting with n-hexane/acet mixtures. 1 H NMR ( MHz), 13 C NMR (100.6 MHz) and 19 F NMR (376.5 MHz) spectra were recorded with a Bruker Avance 400 spectrometer. Infrared (IR) spectra were recorded on a JASC FT/IR-430 spectrophotometer. Mass spectra were determined with a QP2010 Gas Chromatograph Mass spectrometer (EI ion source). Typical Procedure for the Preparation of the 2-Iodohydroxytyrosol Derivative (2a): hydroxytyrosol carbonate 5 (oil; IR (KBr) 2958, 1748, 1496, 1444 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 3 H), 4.29 (t, J = 7.1 Hz, 2 H), 3.78 (s, 3 H), 2.88 (t, J = 7.1 Hz, 2 H), 1.67 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.8, 147.6, 146.2, 130.3, 121.3, 117.8, 109.2, 108.2, 68.7, 54.7, 34.9, 25.9; MS m/z (relative intensity) 252 (11), 178 (54), 161 (100), 136 (28), 77 (25), 59 (28); Anal Calcd for C 13 H 16 5 : C, 61.90; H, 6.39; Found: C, 62.01; H, 6.34) (311 mg, 1.23 mmol), I 2 (313 mg, 1.23 mmol) and Ag 2 S 4 (385 mg, 1.23 mmol) in EtH (15 ml) were stirred for 1 hour at room temperature. After this time, the crude mixture was filtered to eliminate the precipitate of inorganic salt and then washed with a saturated Na 2 S 2 3 solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (Si 2, 35 g, n-hexane/acet 95/5 v/v) to give 441 mg (94% yield) of 2a: mp: C; IR (KBr) 3047, 2967, 2939, 2897, 2868, 1742 cm -1 ; 1 H NMR (CDCl 3 ) δ 7.14 (s, 1 H), 6.69 (s, 1 H), 4.27 (t, J = 7.1 Hz, 2 H), 3.78 (s, 3 H), 3.02 (t, J = 7.1 Hz, 2 H), 1.66 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, 148.4, 147.3, 132.4, 119.1, 118.5, 109.9, 87.3, 67.2, 54.8, 39.7, 25.9; MS m/z (relative intensity) 378 (30), 302 (99), 287 (77), 262 (13), 59 (100); Anal Calcd for C 13 H 15 I 5 : C, 41.29; H, 4.00; Found: C, 41.18; H, Typical Procedure for the Preparation of the 2-Bromohydroxytyrosol Derivative (2b): compound 5 (86 mg, 0.34 mmol), xone (210 mg, 0.34 mmol) and KBr (47 mg, 0.39 mmol) in Acetone (2 ml) and H 2 (2 ml) were stirred for 2 hours at room temperature. After this time, the crude mixture was filtered to eliminate the precipitate of inorganic salts, concentrated under reduced pressure to remove Acetone and finally washed with a saturated Na 2 S 2 3 solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (Si 2, 35 g, n-hexane/acet 95/5 v/v) to give 102 mg (90% yield) of 2b: mp: C; IR (KBr) 3070, 3050, 2994, 2957, 2876, 2855, 1751 cm -1 ; 1 H NMR (CDCl 3 ) δ 6.91 (s, 1 H), 6.66 (s, 1 H), 4.31 (t, J = 7.0 Hz, 2 H), 3.79 (s, 3 H), 3.03 (t, J = (a) 2a: Wah, S. W. Synth. Comm. 1992, 22, (b) 2b: Bovicelli, P.; Bernini, R.; Antonioletti, R.; Mincione, E. Tetrahedron Lett. 2002, 43, (c) 2c: Yanhua, Z.; Kazutaka, S.; Hisashi, Y. Synlett 2005, 2837.
3 S3 Hz, 2 H), 1.67 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, , , 128.8, 119.2, 114.1, 112.6, 110.5, 67.0, 54.8, 35.3, 25.8; MS m/z (relative intensity) 332 (11), 330 (11), 256 (60), 254 (60), 241 (59), 239 (55), 59 (46), 43 (100); Anal Calcd for C 13 H 15 Br 5 : C, 47.15; H, 4.57; Found: C, 47.22; H, Typical Procedure for the Preparation of the 2-Chlorohydroxytyrosol Derivative (2c): compound 5 (655 mg, 2.60 mmol), N-Chlorosuccinimide (411 mg, 3.08 mmol) and AlCl 3 (35 mg, 0.26 mmol) in CH 2 Cl 2 (20 ml) were stirred for 24 hours at room temperature. After this time, Ethyl acetate was added and the resulting mixture was washed with a saturated NaCl solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (Si 2, 100 g, n-hexane/acet 90/10 v/v) to give 633 mg (85% yield) of 2c: oil; IR (KBr) 2992, 2957, 1750, 1490 cm -1 ; 1 H NMR (CDCl 3 ) δ 6.75 (s, 1 H), 6.64 (s, 1 H), 4.31 (t, J = 7.1 Hz, 2 H), 3.79 (s, 3 H), 3.02 (t, J = 7.0 Hz, 2 H), 1.67 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, 147.1, 146.6, 127.0, 125.1, 119.1, 110.3, 109.7, 67.0, 54.8, 32.8, 25.8; MS m/z (relative intensity) 288 (5), 286 (15), 212 (30), 210 (87), 197 (50), 195 (100), 59 (74); Anal Calcd for C 13 H 15 Cl 5 : C, 54.46; H, 5.27; Found: C, 54.54; H, Typical Procedure for the Preparation of 2-Arylhydroxytyrosol Derivatives (3): A Carousel Tube Reactor (Radley Discovery), equipped with a magnetic stirrer, was charged with Pd 2 (dba) 3 (5.7 mg, mmol), SPhos (5.1 mg, mmol) and Dioxane (1 ml). After solubilization of this precatalyst system at room temperature under argon atmosphere, 2c (89 mg, 0.31 mmol) and another amount of Dioxane (1.5 ml) were added to the mixture. After 10 minutes, K 3 P 4 (198 mg, 0.93 mmol) and 4-Acetylphenylboronic acid (76.5 mg, 0.47 mmol) were also added. The resulting mixture was heated at 100 C and stirred for 15 hours. After this time, the mixture was cooled, added with Ethyl acetate, washed with a 0.1 N HCl solution and subsequently with a saturated NaCl solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (Si 2, 30 g, n-hexane/acet 80/20 v/v) to give 100 mg (87% yield) of 3f: oil; IR (KBr) 2991, 2957, 1749, 1685, 1493 cm -1 ; 1 H NMR (CDCl 3 ) δ 7.99 (d, J = 8.0 Hz, 2 H), 7.38 (d, J = 8.0 Hz, 2 H), 6.72 (s, 1 H), 6.59 (s, 1 H), 4.13 (t, J = 7.2 Hz, 2 H), 3.72 (s, 3 H), 2.84 (t, J = 7.2 Hz, 2 H), 2.64 (s, 3 H), 1.70 (s, 6 H); 13 C NMR (CDCl 3 ) δ 197.8, 155.6, 147.4, 146.5, 146.3, 135.7, 134.2, 129.8, 128.4, 127.3, 118.4, 109.8, 109.6, 68.1, 54.7, 32.0, 26.7, 25.9; MS m/z (relative intensity) 370 (2), 294 (3), 165 (3), 77 (10), 59 (100); Anal Calcd for C 21 H 22 6 : C, 68.10; H, 5.99; Found: C, 68.23; H, Analytical Data of 2-Arylhydroxytyrosol Derivatives (3) 3a: mp: C; IR (KBr) 2986, 2957, 2934, 1739, 1489 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 5 H), 6.74 (s, 1 H), 6.65 (s, 1 H), 4.16 (t, J = 7.3 Hz, 2 H), 3.75 (s, 3 H), 2.87 (t, J = 7.3 Hz, 2 H), 1.73 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, 146.9, 146.1, 141.5, 135.5, 129.5, 128.3, 127.3, 126.9,
4 S , 110.2, 109.4, 68.3, 54.7, 32.1, 26.0; MS m/z (relative intensity) 328 (1), 252 (2), 77 (27), 59 (100); Anal Calcd for C 19 H 20 5 : C, 69.50; H, 6.14; Found: C, 69.44; H, b: mp: C; IR (KBr) 3070, 2984, 2958, 2938, 2871, 1757, 1496 cm -1 ; 1 H NMR (CDCl 3 ) δ 7.22 (d, J = 7.9 Hz, 2 H), 7.17 (d, J = 8.0 Hz, 2 H), 6.72 (s, 1 H), 6.62 (s, 1 H), 4.15 (t, J = 7.3 Hz, 2 H), 3.75 (s, 3 H), 2.87 (t, J = 7.3 Hz, 2 H), 2.42 (s, 3 H), 1.72 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, 146.8, 146.0, 138.6, 136.5, 135.4, 129.3, 129.0, 127.3, 118.1, 110.3, 109.4, 68.4, 54.7, 32.2, 26.0, 21.2; MS m/z (relative intensity) 342 (2), 251 (3), 165 (4), 77 (29), 59 (100); Anal Calcd for C 20 H 22 5 : C, 70.16; H, 6.48; Found: C, 70.21; H, c: oil; IR (KBr) 2991, 2956, 2836, 1747, 1608 cm -1 ; 1 H NMR (CDCl 3 ) δ 7.20 (d, J = 8.4 Hz, 2 H), 6.94 (d, J = 8.4 Hz, 2 H), 6.71 (s, 1 H), 6.62 (s, 1 H), 4.14 (t, J = 7.3 Hz, 2 H), 3.86 (s, 3 H), 3.75 (s, 3 H), 2.86 (t, J = 7.3 Hz, 2 H), 1.72 (s, 6 H); 13 C NMR (CDCl 3 ) δ 158.6, 155.7, 146.7, 146.0, 135.1, 133.9, 130.5, 127.4, 118.1, 113.7, 110.4, 109.4, 68.4, 55.3, 54.7, 32.2, 25.9; MS m/z (relative intensity) 358 (3), 267 (2), 251 (2), 77 (8), 59 (100); Anal Calcd for C 20 H 22 6 : C, 67.03; H, 6.19; Found: C, 67.11; H, d: mp: C; IR (KBr) 2993, 2953, 1758, 1495, 1258, 1223 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 4 H), (m, 2 H), (m, 3 H), 6.75 (s, 1 H), 6.68 (s, 1 H), 4.19 (t, J = 7.2 Hz, 2 H), 3.75 (s, 3 H), 2.92 (t, J = 7.3 Hz, 2 H), 1.73 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, 147.1, 146.2, 140.8, 140.5, 139.8, 135.0, 129.9, 128.9, 127.4, 127.2, 127.0, 118.2, 110.2, 109.5, 68.4, 54.7, 32.2, 26.0; MS m/z (relative intensity) 404 (3), 328 (4), 78 (12), 77 (30), 59 (100); Anal Calcd for C 25 H 24 5 : C, 74.24; H, 5.98; Found: C, 74.33; H, e: mp: C; IR (KBr) 2998, 2960, 1753, 1490 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 3 H), 6.71 (s, 1 H), 6.59 (s, 1 H), 4.15 (t, J = 7.3 Hz, 2 H), 3.75 (s, 3 H), 2.84 (t, J = 7.3 Hz, 2 H), 2.32 (s, 3 H), 1.71 (s, 6 H); 13 C NMR (CDCl 3 ) δ (d, J = Hz), 155.7, 147.0, 146.1, (d, J = 15.2 Hz), 134.6, (d, J = 20.4 Hz), (d, J = 31.2 Hz), 127.3, (d, J = 69.6 Hz), 118.2, (d, J = 88.4 Hz), 110.2, 109.4, 68.3, 54.7, 32.1, 25.9, 14.6 (d, J = 13.6 Hz); 19 F NMR (CDCl 3 ) δ ; MS m/z (relative intensity) 360 (2), 269 (3), 183 (3), 77 (35), 59 (100); Anal Calcd for C 20 H 21 F 5 : C, 66.66; H, 5.87; Found: C, 66.52; H, g: mp: C; IR (KBr) 2993, 2953, 2933, 1750, 1720 cm -1 ; 1 H NMR (CDCl 3 ) δ 8.03 (m, 1 H), 7.97 (m, 1 H), (m, 2 H), 6.73 (s, 1 H), 6.61 (s, 1 H), 4.13 (t, J = 7.2 Hz, 2 H), 3.94 (s, 3 H), 3.73 (s, 3 H), 2.83 (t, J = 7.2 Hz, 2 H), 1.72 (s, 6 H); 13 C NMR (CDCl 3 ) δ 167.0, 155.6, 147.3, 146.2, 141.7, 134.3, 133.9, 130.6, 130.3, 128.4, 128.2, 127.3, 118.3, 110.1, 109.5, 68.1, 54.7, 52.2, 32.1, 25.9; MS m/z (relative intensity) 386 (1), 251 (1), 152 (1), 77 (6), 59 (100); Anal Calcd for C 21 H 22 7 : C, 65.28; H, 5.74; Found: C, 65.15; H, h: mp: C; IR (KBr) 3002, 2962, 1752, 1496 cm -1 ; 1 H NMR (CDCl 3 ) δ 7.67 (d, J = 8.1 Hz, 2 H), 7.41 (d, J = 8.1 Hz, 2 H), 6.74 (s, 1 H), 6.60 (s, 1 H), 4.16 (t, J = 7.2 Hz, 2 H), 3.75 (s, 3 H), 2.83 (t, J = 7.1 Hz, 2 H), 1.73 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.6, 147.5, 146.3, (q, J = 5.6 Hz), 133.9, 129.9, (q, J = 30.4 Hz), 127.4, (q, J = 3.7 Hz), (q, J = Hz), 118.5, 109.9, 109.5, 68.2, 54.7, 32.0, 25.9; 19 F NMR (CDCl 3 ) δ -62.3; MS m/z (relative intensity) 395 (3), 77 (23), 69 (22), 59 (100); Anal Calcd for C 20 H 19 F 3 5 : C, 60.61; H, 4.83; Found: C, 60.74; H, 4.89.
5 S5 3i: mp: C; IR (KBr) 3017, 2991, 2969, 2938, 2896, 1755 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 3 H), (m, 1 H), 6.71 (s, 1 H), 6.50 (s, 1 H), (m, 2 H), 3.72 (s, 3 H), (m, 1 H), (m, 1 H), 2.08 (s, 3 H), 1.72 (s, 3 H), 1.70 (s, 3 H); 13 C NMR (CDCl 3 ) δ 155.6, 146.8, 146.1, 140.8, 136.3, 134.5, (2 C), 127.5, 127.4, 125.6, 118.0, 109.7, 109.3, 68.1, 54.6, 32.1, 26.0, 20.0; MS m/z (relative intensity) 342 (2), 251 (3), 165 (4), 77 (24), 59 (100); Anal Calcd for C 20 H 22 5 : C, 70.16; H, 6.48; Found: C, 70.03; H, j: mp: C; IR (KBr) 3111, 2985, 2959, 1739, 1495, 1272 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 1 H), (m, 1 H), (m, 1 H), 6.71 (s, 1 H), 6.68 (s, 1 H), 4.19 (t, J = 7.2 Hz, 2 H), 3.76 (s, 3 H), 2.91 (t, J = 7.2 Hz, 2 H), 1.71 (s, 6 H); 13 C NMR (CDCl 3 ) δ 155.7, 147.1, 146.1, 141.5, 129.9, 129.2, 127.9, 125.3, 122.7, 118.2, 110.2, 109.5, 68.3, 54.7, 32.3, 26.0; MS m/z (relative intensity) 334 (4), 258 (9), 187 (8), 172 (8), 115 (11), 77 (18), 59 (100); Anal Calcd for C 17 H 18 5 S: C, 61.06; H, 5.43; Found: C, 60.92; H, Preparation of (6a): Compound 3a (80 mg, 0.24 mmol) and TsH H 2 (46 mg, 0.24 mmol) in CN (0.8 ml) and H 2 (0.2 ml) were stirred for 6 h at 80 C. After this time, ethyl acetate was added and the resulting mixture was washed with a saturated NaHC 3 solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (Si 2, 35 g, n-hexane/acet 60/40 v/v) to give 58 mg (80% yield) of 6a: viscous oil: IR (KBr) 3390, 1732, 1448 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 3 H), (m, 2 H), 6.86 (s, 1 H), 6.78 (s, 1 H), (bs, 2 H), 4.14 (t, J = 7.2 Hz, 2 H), 3.74 (s, 3 H), 2.85 (t, J = 7.2 Hz, 2 H); 13 C NMR (CDCl 3 ) δ 156.0, 143.1, 142.2, 141.0, 135.4, 129.4, 128.3, 127.0, 126.9, 117.4, 116.7, 68.5, 54.9, 31.6; Anal Calcd for C 16 H 16 5 : C, 66.66; H, 5.59; Found: C, 66.52; H, Preparation of (7a): Compound 3a (88 mg, 0.27 mmol) and K 2 C 3 (112 mg, 0.81 mmol) in DMF (0.8 ml) and H 2 (0.2 ml) were stirred for 24 h at 80 C. After this time, ethyl acetate was added and the resulting mixture was washed with a 0.1 N HCl solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue was purified by chromatography (Si 2, 35 g, n-hexane/acet 75/25 v/v) to give 66 mg (92% yield) of 7a: mp: C; IR (KBr) 3317, 3053, 2979 cm -1 ; 1 H NMR (CDCl 3 ) δ (m, 2 H), (m, 1 H), (m, 2 H), 6.74 (s, 1 H), 6.65 (s, 1 H), 3.64 (t, J = 6.9 Hz, 2 H), 2.77 (t, J = 6.9 Hz, 2 H), 1.73 (s, 6 H), 1.63 (bs, 1 H); 13 C NMR (CDCl 3 ) δ 146.9, 145.9, 141.8, 135.4, 129.6, 128.4, 128.2, 126.8, 118.1, 110.3, 109.4, 63.6, 36.1, 26.0; Anal Calcd for C 17 H 18 3 : C, 75.53; H, 6.71; Found: C, 75.67; H, Preparation of (8a): Compound 7a (80 mg, 0.30 mmol) and TsH H 2 (56 mg, 0.30 mmol) in CN (0.8 ml) and H 2 (0.2 ml) were stirred for 5 h at 80 C. After this time, ethyl acetate was added and the resulting mixture was washed with a saturated NaHC 3 solution. The organic phase was separated, dried over Na 2 S 4, filtered and concentrated under reduced pressure. The residue
6 was purified by chromatography (Si 2, 35 g, n-hexane/acet/h 55/45/5 v/v/v) to give 59 mg (87% yield) of 8a: mp: C; IR (KBr) 3429, 2952 cm -1 ; 1 H NMR (DMS d6 ) δ (m, 2 H), (m, 2 H), (m, 3 H), 6.72 (s, 1 H), 6.57 (s, 1 H), 4.53 (t, J = 4.9 Hz, 1 H), (m, 2 H), 2.56 (t, J = 7.4 Hz, 2 H); 13 C NMR (DMS d6 ) δ 145.0, 143.7, 142.2, 133.2, 129.7, 128.5, 127.3, 126.8, 117.6, 117.5, 62.8, 36.1; Anal Calcd for C 14 H 14 3 : C, 73.03; H, 6.13; Found: C, 73.12; H, S6
7 NMR Spectra S7
8 S8 5 C 2
9 S9 5 C 2
10 S10 2a I C 2
11 S11 2a I C 2
12 S12 2b Br C 2
13 S13 2b Br C 2
14 S14 2c Cl C 2
15 S15 2c Cl C 2
16 S16 3a C 2
17 S17 3a C 2
18 S18 3b C 2
19 S19 3b C 2
20 S20 3c C 2
21 S21 3c C 2
22 S22 3d C 2
23 S23 3d C 2
24 S24 3e C 2 F
25 S25 3e C 2 F
26 S26 3e C 2 F
27 S27 3f C 2 C
28 S28 3f C 2 C
29 S29 3g 2 C C 2
30 S30 3g 2 C C 2
31 S31 3h C 2 F 3 C
32 S32 3h C 2 F 3 C
33 S33 3h C 2 F 3 C
34 S34 3i C 2
35 S35 3i C 2
36 S36 3j S C 2
37 S37 3j S C 2
38 S38 H H 6a C 2 CH 3
39 S39 6a H H C 2 CH 3
40 S40 7a H
41 S41 7a H
42 H H S42 8a H
43 H H S43 8a H
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