Methanesulfonyl chloride → Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate

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To a mixture of methyl 4-amino-1H-indole-6-carboxylate (1.0 g) in DMF (10 mL) was added 4-dimethylaminopyridine (1.46 g) and methanesulfonyl chloride (0.6 g). The mixture was heated to 60° C. for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed three times with brine, dried over anhydrous sodium sulfate and concentrated to give 0.71 g of the title compound: 1H NMR (CDCl3) δ 3.02, 3.94, 6.69, 7.42, 7.81, 8.04.

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