Sodium hydride → 1-(3-bromo-6-methoxy-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol

반응식

[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3.[O:19]1[CH2:21][CH:20]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:21][CH:20]([OH:19])[CH2:22][NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3

참가 물질

실험 절차

NaH (0.0023 g of 60% suspension (in oil), 0.093 mmol) was added to a solution of 3-bromo-6-methoxy-9H-carbazole (0.014 g, 0.052 mmol) in anhydrous THF (0.1 mL) at 0° C. and stirred for 30 min. A solution of N-(oxiran-2-ylmethyl)aniline (0.0093 g, 0.062 mmol) in anhydrous THF (0.1 mL) was added dropwise to the reaction mixture. The reaction was warmed to room temperature and stirred for 48 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organics were concentrated and purified by chromatography (SiO2, 0-30% EtOAc/Hexane) to afford the title compound (0.007 g, 25%).