Benzenesulfonyl chloride → HCID 57473900, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 40 mg (0.18 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 30 μL (0.23 mmol) of benzenesulfonyl chloride in 1 mL of pyridine was warmed at 45° C. The reaction was monitored by TLC (ethyl acetate-hexanes (25:75)) indicating a new less polar product compared to amine. The mixture stirred for 18 hours at 45° C. and over the weekend at room temperature. The mixture was diluted with 7 mL of 1 N aqueous HCl and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of 1 N aqueous HCl, 5 mL of brine, and three 5 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed onto silica gel and chromatographed on silica gel using dichloromethane-hexanes (gradient 50-100%). The material from the column solidified from ether-hexanes to afford 44 mg (68%) of the title compound as an white solid, m.p. 121° C.-123° C., MS: m/z 367.08 (M−).

Provenance & Evidence