m-Chloroperbenzoic acid → benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxide

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Reaction Steps

A stirred suspension of benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1 g, 3.9 mmol, Step a)) in a mixture of dichloromethane and dimethyl ether (10:1 mL) was treated portion wise with 3-chloroperoxybenzoic acid (0.85 g, 4.9 mmol) followed by stirring at room temperature for 4 hours. The reaction was neutralized with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to yield benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate 5-oxide (1 g, 99%).

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