Potassium Carbonate → 3-(5-amino-2-methyl-phenyl)-7-chloro-1-phenyl-1H-[1,6]naphthyridin-2-one

Participants

Reaction Conditions

Reaction Steps

6-Chloro-4-phenylamino-pyridine-3-carbaldehyde 18 (21 mg, 0.09 mmol) is mixed with 2-(5-amino-2-methyl-phenyl)acetic acid methyl ester 7 (18 mg, 0.1 mmol) and potassium carbonate (37 mg, 0.27 mmol) in DMF (2 mL). The mixture is heated to 100° C. for 16 h. After cooling to rt and removing solvent in vacuo, the crude product is purified using flash chromatography (hexane:ethyl acetate=1:1). The title compound 3-(5-amino-2-methyl-phenyl)-7-chloro-1-phenyl-1H-[1,6]naphthyridin-2-one 19 is obtained as a pale solid. 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 7.68 (s, 1H), 7.53-7.57 (m, 2H), 7.47-7.51 (dt 1H), 7.20-7.23 (m, 2H), 6.96 (d, 1H), 6.59 (dd, 1H), 6.58 (s, 1H), 6.52 (s, 1H), 2.05 (s, 3H).

Provenance & Evidence