Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate → Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

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Reaction Steps

A stirred solution of ethyl-α-azido-β-(4-methoxypyrid-3-yl)-acrylate 2 (3.7 g, 14.9 mmol) in dry o-xylene (35 mL) was heated in an oil bath at 170° C. for 25 min. During this time the contents of the flask gained brick red color. After cooling, the mixture was concentrated under high vacuum. The resultant brown residue was purified on silica gel column using 5% methanol in CH2Cl2 to give 3 as brick red solid. Mp 195-197° C.; Yield: 3.3 g, 82%; ESI MS: m/z 220.9 (M+1).

Provenance & Evidence