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

Reaction equation

[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]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 27362561,2-Dimethylimidazole-4-sulfonyl chloride

HCID 68715707(5-Methoxy-1H-indol-4-ylmethyl)-dimethyl-amine2×

Product 1

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

Procedure

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)+.