Indole → N-{3-[4-(1H-indol-1-ylmethyl)phenyl]pyrazin-2-yl}-2-(trifluoromethyl)benzenesulfonamide

Participants

Reaction Steps

To a solution of 1H-Indole (234 mg, 2.0 mmol, 1 eq) in dimethylformamide (10 mL) was added sodium hydride (80 mg, 2 mmol, 1 eq). After the evolution of hydrogen ceased, N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}-2-(trifluoromethyl)benzene sulfonamide (intermediate 26) (854 mg, 2 mmol, 1 eq) in dimethylformamide (5 mL) was added and the reaction mixture heated to 80 degrees over 3 hours. The reaction was cooled, diluted with 30 mL of water and extracted with diethyl ether. The organic layer was dried over MgSO4, evaporated and purified by flash chromatography on silica gel eluting with AcOEt and cyclohexane to give pure N-{3-[4-(1H-indol-1-ylmethyl)phenyl]pyrazin-2-yl}-2-(trifluoromethyl)benzenesulfonamide as a yellow solid (630 mg, 1.24 mmol, yield: 62%, 97% HPLC purity).

Provenance & Evidence