Triethylsilane → Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate

Participants

Reaction Steps

TMSOTf (3.38 mL, 18.7 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran-4-one (2.17 g, 18.7 mmol) in DCM (100 mL) at 0° C. (bath temp) under nitrogen. A solution of ethyl 5-bromo-1H-indole-7-carboxylate (5 g, 18.7 mmol) in DCM (30 mL) was then added and the reaction was stirred for 30 min. Triethylsilane (4.47 mL, 28.1 mmol) was added and the reaction was allowed to warm to room temperature overnight. The reaction mixture was washed with saturated aqueous Na2CO3 (1×100 mL, and the organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was washed with MeOH, giving 4.92 g (72%) of the title compound.

Provenance & Evidence