Benzenesulfonyl chloride → Indole

Participants

Reaction Conditions

Reaction Steps

NaH (600 mg, 15.00 mmol) was added (in several batches) to a solution of 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (3 g, 9.79 mmol) in DMF (60 mL) while cooling to a temperature of 0-5° C. The resulting solution was stirred for 1 hour while the temperature was maintained at room temperature. Benzenesulfonyl chloride (2.3 g, 12.89 mmol) was then added dropwise and the reaction was stirred for an additional 4 hours at room temperature. After filtration, the filter cake was washed with ethanol (2×50 mL) and the resulting solid was dried to afford 0.4 g (10%) of 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-phenylsulfonyl)-1H-indole as a white solid. 1H NMR (DMSO) δ 8.04 (4H), 7.95 (1H), 7.73 (1H), 7.32-7.63 (3H), 6.29 (s, 1H), 3.98 (2H), 3.68 (2H), 2.72-2.89 (5H). m/z 434.1 (M++1)

Provenance & Evidence