Methyl iodide → Methyl 3-methoxy-4-((1-methyl-5-nitro-1H-indol-3-yl)methyl)benzoate

Participants

Reaction Steps

Sodium hydride (212 milligrams) was added to a solution of methyl 3-methoxy-4-(5-nitroindol-3-ylmethyl)benzoate (1.8 grams) in 60 mL of dry tetrahydrofuran. After stirring for 10 minutes, methyl iodide (753 milligrams) was added and the reaction was stirred at room temperature for 2 hours. The volatiles were evaporated and the residue dissolved in ethyl acetate. The ethyl acetate layer was washed with water, dried over sodium sulfate and evaporated. The residue was purified on silica gel with dichloromethane to give 1.8 grams product, m.p. 151°-153°.

Provenance & Evidence