Methyl iodide → HCID 11544946, compound

Participants

Reaction Steps

To a 0° C. tetrahydrofuran solution of 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester (0.500 g, 1.40 mmol) was added sodium hydride (95%, 0.037 g, 1.54 mmol) followed by iodomethane (0.096 mL, 1.54 mmol). 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester was synthesized in a manner analogous to Intermediate 1, using benzene thiol instead of 2-methyl benzenethiol. N,N-Dimethylformamide was added to homogenize the reaction. The reaction was allowed to warm to room temperature and stir overnight. The reaction was diluted with ethyl acetate (100 mL). The organic layers were washed with 1N hydrochloric acid (25 mL) and brine (25 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title product, which was used without further purification.

Provenance & Evidence