Methyl iodide → Ethyl 6-cyano-1-methyl-1h-indole-2-carboxylate

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Reaction Steps

Treat a solution of 6-cyano-1H-indole-2-carboxylic acid ethyl ester (86 mg, 0.40 mmol) in THF (3 mL) with sodium hydride (60% disp. in mineral oil, 18 mg, 0.44 mmol) under N2. After stirring for 10 min, add iodomethane (68 mg, 0.48 mmol) and stir at rt for 3 h. Quench the reaction with sat. NH4Cl solution and extract several times with EtOAc. Dry the combined organic layers (Na2SO4) and concentrate to give a solid. Purify the crude product by silica gel chromatography (MeOH/DCM: 0% to 10%) to give the desired 6-cyano-1-methyl-1H-indole-2-carboxylic acid ethyl ester in 59% yield (54 mg, 0.24 mmol).

Provenance & Evidence