Dichloromethane → N-cyclohexyl-N-thiazol-2-yl-1-(2-chlorobenzoyl)-5-hydroxy-2-methylindole-3-acetamide

反応式

[CH:1]1([N:7]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[C:8](=[O:31])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19]C)[CH:17]=3)[N:12]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25](Cl)=[CH:24][CH:23]=3)[C:11]=2[CH3:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.[Cl:41]CCl>>[CH:1]1([N:7]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[C:8](=[O:31])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=3)[N:12]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:41])[C:11]=2[CH3:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

反応物 3

HCID 6344Dichloromethane

HCID 25134Boron tribromide

HCID 58618036N-cyclohexyl-N-thiazol-2-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide

生成物 1

HCID 69311092N-cyclohexyl-N-thiazol-2-yl-1-(2-chlorobenzoyl)-5-hydroxy-2-methylindole-3-acetamide

実験手順

To a solution of 2 g (3.83 mmol) of N-Cyclohexyl-N-thiazol-2-yl-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide in 20 mL of anhydrous dichloromethane under nitrogen at −78° C. was added dropwise 1.1 mL (11.5 mmol) of boron tribromide over 15 minutes. The reaction was allowed to warm to room temperature and stirred for 20 hr before quenching with water (5 mL). The layers were separated and the organic layer dried (Na2SO4), filtered and evaporated. The residue was chromatographed on silica to give the title compound. 1H NMR (DMSO) δ 9.24 (1H, s), 7.79 (2H, bs), 7.70 (4H, m), 6.87 (1H, d), 6.81 (1H, d), 6.59 (1H, dd), 4.43 (1H, bs), 3.40 2.08 (1H, m), 1.77 (4H, m), 1.61 (1H, m), 1.32 (4H, m). 5H concealed by DMSO and water signals.