Triethylsilane → 5-bromo-3-(2,2-dimethyltetrahydro-thiopyran-4-yl)-1H-indole-7-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of 2,2-Dimethyl-tetrahydro-thiopyran-4-one (7.9 g, 55.1 mmol) in DCM (100 mL) was added TMSOTf (10 mL, 55.1 mmol) and 5-Bromo-1H-indole-7-carboxylic acid methyl ester (7.0 g, 27.6 mmol) at 0° C. After 2 hours, Et3SiH (15 mL, 110 mmol) was added at 0° C., then the mixture was stirred for 18 hours. The reaction mixture was quenched with sat. Sodium bicarbonate solution, extracted with DCM (3×100 mL). The combined organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (PE:EA=50:1 to 30:1) to give the title compound as a light yellow solid (5.5 g, 52%).

Provenance & Evidence