Methyl Acrylate → methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 3-bromo-6-(dibenzylamino)pyridine-2-carboxylate (3.16 g, 7.68 mmol), palladium acetate (172 mg, 0.768 mmol), triphenylphosphine (404 mg, 1.54 mmol), potassium carbonate-(1.59 g, 11.5 mmol) and methyl acrylate (1.21 mL, 15.4 mmol) in N,N-dimethylformamide (77 mL) was stirred with heating at 120° C. for 12 hr. The reaction solution was diluted with diethyl ether, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (2.60 g, yield 81%).

Provenance & Evidence