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

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Reaction Steps

To a solution of tetrahydro-thiopyran-4-carbaldehyde (1.3 g, 9.84 mmol) in DCM (20 mL) was added TMSOTf (3.5 mL, 19.7 mmol) at 0° C. To this mixture 5-Bromo-1H-indole-7-carboxylic acid methyl ester (2.5 g, 9.84 mmol) was added. After 2 hours, Et3SiH (6.2 mL, 39.4 mmol) was added at 0° C., and stirring continued for 18 hours. The reaction mixture was quenched with sodium bicarbone solution and extracted with DCM. The combined organic layers were dried (MgSO4), concentrated, and purified by column chromatography on silica gel, giving 1.6 g (44%) of the title compound.

Provenance & Evidence