2,6-Dichloro-4-(trifluoromethyl)benzenesulfonyl chloride → 2,6-Dichloro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]4-trifluoromethylbenzenesulfonamide

Participants

Reaction Steps

A mixture of 100 mg (0.44 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 137 mg (0.44 mmol) of 2,6-dichloro-4-(trifluoromethyl)benzenesulfonyl chloride in 8 mL of pyridine was stirred at room temperature for 2 hours, and warmed at 70° C. for 18 hours. The mixture was cooled to room temperature and diluted with 1 M HCl until acidic and extracted with ethyl acetate. The combined organic layers were washed with 1 N aqueous HCl, saturated aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, decanted, and concentrated in vacuo. The crude material was crystallized from ether-hexanes to afford 40 mg (18%) of the title compound as a colorless powder. MS: m/z 505 (M), 507 (M+2).

Provenance & Evidence