Ethanol → Ethyl 5-[(tert-butoxycarbonyl)amino]-3-chloropyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(N-(tert-butoxycarbonyl)amino)-5,6-dichloropyridine (2.7 g) in anhydrous ethanol (50 ml) were added anhydrous triethylamine (7.38 g), palladium acetate (1.75 g) and 1,3-bis(diphenylphosphino)propane (3.21 g). The inside of the reaction vessel was substituted for 1 atm. carbon monoxide and the mixture was stirred at 60° C. After 10 hr, ethyl acetate (250 ml) was added to the reaction mixture, and an insoluble matter was filtered off. The filtrate was concentrated and the residue was applied to flash silica gel column chromatography (silica gel, 500 ml) and eluted with hexane:ethyl acetate=10:1-5:1-3:1-2:1 to give ethyl 5-(N-(tert-butoxycarbonyl)amino)-3-chloropyridine-2-carboxylate as a colorless solid (5.85 g).

Provenance & Evidence