Butyl Acrylate → butyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

A mixed solution of 150 mL of butyl acetate and 73 mL of butyl acrylate was refluxed with heating for 45 minutes under a nitrogen atmosphere. The reaction mixture was cooled to 30° C., 50.0 g of 2-chloro-5-fluoropyridine-3-amine, 3.8 g of palladium (II) acetate, 44.8 g of triphenylphosphine and 36.6 g of sodium carbonate were added thereto, and the mixture was refluxed for 13 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, 150 mL of water and 700 mL of butyl acetate were added thereto, and the mixture was stirred for 1 hour. Insoluble matter was filtered out, and the filter residue was washed using 50 mL of butyl acetate. The filtrate and the wash liquid were combined, the organic layer was separated, and 800 mL of the solvent was evaporated under reduced pressure. To the obtained residue, 300 mL of cyclohexane and 30 mL of toluene were added dropwise, the mixture was cooled to 5° C., and the solid product was obtained by filtration and washed using a mixed solution of toluene-cyclohexane (1:2) and toluene to give 57.8 g of butyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate as a yellow solid.

Provenance & Evidence