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

Participants

Reaction Steps

To a solution of 50 mg (0.18 mmol) of 2,4-dichloro-6-methoxybenzenesulfonyl chloride in 4 mL of pyridine was added 42 mg (0.19 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine. The mixture stirred for 6 hours at room temperature and was then diluted with 10 mL of ethyl acetate and washed with four 30 mL portions of 10% acetic acid, two 30 mL portions of saturated aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, decanted and concentrated in vacuo. The crude material was purified by filtering through a pad of silica eluting with ether. The material from the pad was dissolved in ether, and precipitated by slow evaporation which afforded 50 mg (57%) of the title compound as a bright yellow powder. MS: m/z 467 (M+1).

Provenance & Evidence