Potassium Carbonate → 8-(3-Methoxy-phenyl)-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

Methyl 6-amino-5-bromonicotinate (500 mg, 2.16 mmol), 2-methoxycarbonylphenylboronic acid (580 mg, 3.25 mmol), palladium(II) acetate (20 mg, 0.09 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (70 mg, 0.17 mmol), and potassium carbonate (900 mg, 6.50 mmol) were dissolved in dioxane/H2O (11 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a membrane plug, and purified via prep-LC-MS to provide 21 (60 mg, 11% yield) as a white solid. LC-MS (M+H=241, obsd.=241). 1H NMR (400 MHz, d6-DMSO): δ 8.98 (d, 1H), 8.87 (d, 1H), 8.48 (d, 1H), 8.32 (dd, 1H), 7.88 (t, 1H), 7.65 (t, 1H).

Provenance & Evidence