Triethylamine → tert-Butyl [[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]carbamate

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Reaction Steps

The 5-azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine (230 mg, 0.529 mmol) obtained in Example 62 and palladium carbon (46 mg) were added to a mixture of ethyl acetate (15 ml) and ethanol (15 ml). The resulting mixture was stirred for 45 minutes under a hydrogen atmosphere of 1 atmospheric pressure. The reaction mixture was filtered. The filtrate was then concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane (5 ml). To the resulting solution were added triethylamine (70 μl, 0.499 mmol) and di-t-butyl carbonate (174 mg, 0.996 mmol). The resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography, and the fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure to give the title compound (78 mg, 0.153 mmol, 37%) as a colorless amorphous substance.

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