Methyl iodide → methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Participants

Reaction Steps

To a stirred solution of methyl 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (910 mg, 4.41 mmol) in N,N-dimethylformamide (35 ml) at room temperature under a nitrogen atmosphere was added slowly sodium hydride (60 w/w % in mineral oil, 177 mg, 4.41 mmol). After 30 minutes iodomethane (0.302 ml, 4.85 mmol) was added and the reaction mixture was stirred at room temperature for 1.5 hours. Then the reaction was quenched in water and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (gradient of heptane to heptane/ethyl acetate 1/1) to give methyl 5-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (878 mg).

Provenance & Evidence