SR 13668 → HCID 59238928、化合物
反応式
[CH3:1][O:2][C:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([C:16](OCC)=O)=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]2[C:21]3[CH:22]=[C:23]([C:28](OCC)=O)[CH:24]=[CH:25][C:26]=3[NH:27][C:4]=12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[C:4]2[NH:27][C:26]3[C:21](=[CH:22][C:23]([CH3:28])=[CH:24][CH:25]=3)[C:5]=2[CH:6]=[C:7]2[C:8]3[CH:9]=[C:10]([CH3:16])[CH:11]=[CH:12][C:13]=3[NH:14][C:15]=12参加物
4
実験手順
To a solution of diethyl 6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxylate (1.72 g, 4 mmol) in THF (40 mL), with stirring at 0-5° C. and under Ar, was slowly added a solution of LAH in THF (16 mL, 1.0 M). After addition of LAH solution, the mixture was warmed to room temperature and then refluxed 2 h. The reaction mixture was cooled in an ice-water bath and quenched by carefully adding ethyl acetate (20 mL) and water (20 mL). The resultant mixture was extracted with ethyl acetate (3×100 ml); the extracts were combined, washed with brine, dried over Na2SO4, filtered, and evaporated to dryness. The residue was subjected to chromatography on silica gel to give 6-methoxy-2,10-dimethyl-5,7-dihydroindolo[2,3-b]carbazole (180 mg, 14%), 1H NMR (400 MHz, DMSO-d6) δ ppm 10.97 (s, 2H), 8.45 (s, 1H), 7.91 (s, 2H), 7.33 (d, J=8.0 Hz, 2H), 7.14 (dd, J=1.2, 8.0 Hz, 2H), 4.07 (s, 3H), 2.49 (s, 6H).