Ethyl Acrylate → 7-Fluoro-1,5-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To 0.99 g of 2-bromo-5-fluoropyridin-3-amine, 0.67 mL of ethyl acrylate, 3.5 mL of triethylamine, and 0.13 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 145 to 150° C. for 5 hours in a sealed tube. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=100:0 to 90:10 to obtain 0.37 g of ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate and 0.15 g of 7-fluoro-1,5-naphthyridin-2(1H)-one as light brown solids.

Provenance & Evidence