Methyl iodide → 2-[3-(6-Chloro-2-methyl-1-pyridin-3-yl-1H-indol-3-ylsulfanyl)-phenyl]-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide (10.7 mmol) in THF (10 mL), freshly prepared at −78° C., was added to a solution of ([3-(6-Chloro-2-methyl-1-pyridin-3-yl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid ethyl ester (0.256 g, 0.586 mmol) in THF (5 mL) at −78° C. The reaction was stirred at −78° C. for 2 hours then iodomethane (0.044 mL, 0.71 mmol) was added and the reaction was allowed to warm to 0° C. After stirring at 0° C. for 30 minutes the reaction was submitted to standard aqueous workup then purified by silica gel chromatography (0-30% EtOAc in hexanes) to yield the title compound.

Provenance & Evidence