Methanol → Methyl 5-methoxy-1H-pyrrolo[2,3-C]pyridine-2-carboxylate

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Reaction Steps

To 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1 g, 5.20 mmol) in methanol (100 ml) was added sulfuric acid (0.014 ml, 0.260 mmol). The resulting solution was heated to reflux and stirred at this temperature overnight. Then extra sulfuric acid (0.277 ml, 5.20 mmol) was added and heated at reflux for five days. The heating was stopped and the reaction mixture was concentrated to a smaller volume. The resulting suspension was diluted with ethyl acetate and washed with an aqueous saturated sodium hydrogen carbonate solution. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give methyl 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (910 mg).

Provenance & Evidence