2,4,6-Trifluorobenzenesulfonyl chloride → 2,4,6-Trifluoro-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

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A mixture of 100 mg (0.44 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 101 mg (0.44 mmol) of 2,4,6-trifluorobenzenesulfonyl 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 then cooled to room temperature and diluted with 1 N aqueous HCl until acidic and extracted with ethyl acetate. The combined organic layers was 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 (21%) of the title compound as a colorless powder. MS: m/z 423 (M+1).

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