Azobisisobutyronitrile → 1-Benzenesulfonyl-2-bromomethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

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Reaction Steps

To 1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (0.27 g, 0.88 mmol) in 1,2-dichloroethane (5.0 mL) was added NBS (0.178 g, 1.00 mmol) and AIBN (0.032 g, 0.20 mmol and the reaction mixture was heated under reflux for 1 h. After cooling to ambient temperature the solvent was removed by evaporation and the resultant residue was purified by flash chromatography (silica, 5 g column, ISCO, 0-65% DCM in pentane) to afford the title compound as a white solid (0.26 g, 72%). LCMS (Method B): RT=3.95 min, M+H+=409/411.

Provenance & Evidence