Methyl Acrylate → (E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylate

Participants

Reaction Steps

A solution of 3-amino-2-bromo-5-chloropyridine (2.257 ml, 19.96 mmol), Reactant 2 (0.283 g, 0.399 mmol), triethylamine (3.03 g, 29.9 mmol) and methyl acrylate (3.44 g, 39.9 mmol) in 5 mL of DMF was heated at 145° C. under microwave irradiation for 35 min. The reaction mixture was evaporated to dryness and was loaded to flash column (DCM to DCM/EA=10:1) to give 1.98 g of pure (E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylate (2.7 g, 12.70 mmol, 63.6% yield) as a light yellow solid and 820 mg of less pure product. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.01 (d, J=1.8 Hz, 1H), 7.72 (d, J=15.1 Hz, 1H), 7.01 (d, J=2.0 Hz, 1H), 6.92 (d, J=15.3 Hz, 1H), 4.02 (br. s., 2H), 3.81 (s, 3H).

Provenance & Evidence