Methanol → Methyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)-8-oxo-5,6,7,8-tetrahydro-1,7-naphthyridine-2-carboxylate

Participants

Reaction Steps

A mixture of tert-butyl 4-((2-(2,6-dichloropyridin-3-yl)ethyl)amino)piperidine-1-carboxylate (10.5 g), a dichloromethane adduct of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.30 g), triethylamine (11.8 mL), methanol (20 mL), and DMF (60 mL) was stirred at 90° C. for 7 hours in a carbon monooxide (5 atm) atmosphere. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (4.01 g).

Provenance & Evidence