Water → HCID 20084251, compound

Participants

Reaction Steps

To a solution of ethyl 5-methoxy-3-(t-butylthio)indole-2-carboxylate from step 1 in DMF (50 ml) at 0° C. was added sodium hydride (60% suspension in mineral oil 460 mg, 11.5 mmol). The reaction mixture was stirred at room temperature for 15 minutes, and p-chlorobenzyl chloride (1.93 g, 12.0 mmol) was added. The reaction mixture was stirred at ambient temperature for 14 hours and was then poured into H2O (200 ml) and extracted with ethyl acetate. The organic phase was washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (8:1 hexane/ethyl acetate) to provide 4.1 g of ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindole-2-carboxylate.

Provenance & Evidence