反应详情

To a solution of sodium methanolate (61 mg, 1.1 mmol, 1.4 eq.) in anhydrous ethanol (10 mL) were added, under an argon atmosphere, (5-methoxy-1H-indol-3-yl)-acetonitrile (150 mg, 0.8 mmol, 1.0 eq.) and, after 30 minutes stirring, 2,4-dimethoxy-benzaldehyde (200 mg, 1.2 mmol, 1.5 eq.). The reaction apparatus was protected from light and the mixture stirred at room temperature for 3 days. The solvent was removed under reduced pressure and the residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 100:0 to 98:2) to afford, after trituration with diethyl ether, the compound (14) as a yellow powder (85 mg, 32%). TLC: Rf=0.55 (CH2Cl2 96/EtOH, 4); mp: 141° C.; IR νmax (cm-1): 2212 (νCN), 3400 (νN—H); 1H NMR (DMSO, 300 MHz): δ (ppm): 3.81 (6H, s, 3″-methoxy and 5″-methoxy), 3.82 (3H, s, 5′-methoxy), 6.58 (1H, s, H4″), 6.89 (1H, dd, J6′-7′=8.9 Hz, J6′-4′=2.1 Hz, H6′), 7.11 and 7.12 (2H, m, H2″ and H6″), 7.39 (1H, d, J7′-6′=8.9 Hz, H7′), 7.44 (1H, d, J4′-6′=2.1 Hz, H4′), 7.64 (1H, s, H2′), 7.74 (1H, s, H3), 11.60 (1H, s, H indolic H); 13C NMR (DMSO, 75.5 MHz): δ (ppm): 55.8 (3″-methoxy and 5″-methoxy), 56.0 (5′-methoxy), 101.8 (C4′), 102.3 (C4″), 106.7 (C2), 107.0 (C2″ and C6″), 110.7 (C3′), 112.7 (C6′), 113.6 (C7′), 118.9 (C1), 124.5 (C3a′), 127.6 (C2′), 132.7 (C7a′), 136.5 (C3), 136.9 (C1″), 154.9 (C5′), 161.0 (C3″ and C5″); ESI-MS: m/z 357.1 ([M+Na]+); HRESI-MS: m/z 357.1219 (calcd for C20H18N2O3Na, 357.1205); Anal. Calcd for C20H18N2O2, 0.2H2O: C, 71.08; H, 5.49; N, 8.29; O, 15.15. Found: C, 70.89; H, 5.23; N, 8.34.

1. customThe solvent was removed under reduced pressure
2. customthe residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 100:0 to 98:2)
3. customto afford