Triethylsilane → HCID 59332568, compound

Participants

Reaction Steps

To the stirred mixture of dihydro-3(2H)-thiophenone (0.167 mL, 1.97 mmol) in DCM (25 mL) under N2 was added TMS-OTf (0.71 mL, 3.9 mmol) slowly over about 5 minutes at 0° C. (ice-bath). A solution of ethyl 5-bromo-1H-indole-7-carboxylate (0.50 g, 1.97 mmol) in DCM (5 mL) was added dropwise over 60 min, then triethylsilane (1.26 mL, 9.8 mmol) was added in one portion, and the reaction was allowed to warm slowly to room temperature. Then saturated NaHCO3 and DCM were added, the layers were separated and the aqueous layer was extracted with DCM twice. The combined organic layers were dried (MgSO4) and concentrated. The residue was purified using Companion, giving 312 mg (46%) of the title compound.

Provenance & Evidence