Dimethylformamide → 1-{1-[(1,2-Dimethyl-1H-imidazol-4-yl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine

반응식

[CH3:1][O:2][C:3]1[C:4]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.CN(C=O)C.[CH3:21][N:22]1[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:24]=[C:23]1[CH3:31]>>[CH3:21][N:22]1[CH:26]=[C:25]([S:27]([N:8]2[C:9]3[C:5](=[C:4]([CH2:12][N:13]([CH3:14])[CH3:15])[C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)(=[O:29])=[O:28])[N:24]=[C:23]1[CH3:31]

참가 물질

반응물 3

HCID 6228Dimethylformamide

HCID 27362561,2-Dimethylimidazole-4-sulfonyl chloride

HCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2회

생성물 1

HCID 595135511-{1-[(1,2-Dimethyl-1H-imidazol-4-yl)sulfonyl]-5-methoxy-1H-indol-4-yl}-N,N-dimethylmethanamine수율 15.8%

실험 절차

To a solution of 1-(5-methoxy-1H-indol-4-yl)-N,N-dimethylmethanamine (15 mg, 0.07 mmol; Intermediate 97) in DMF (1 mL) NaH (4 mg, 0.15 mmol) was added at rt. The reaction mixture was stirred at rt for 15 min and 1,2-dimethyl-1H-imidazole-4-sulfonyl chloride (21 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at rt over night. The reaction was quenched by addition of water. Purification by preparative HPLC/UV (System B) afforded the title product (4 mg, 14%) as a brown solid. MS (ESI+) for C17H22N4O3S m/z 386 (M+H)+.