Potassium Carbonate → 5H-Benzo(c)(1,8)naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

2-Amino-3-iodo-5-bromopyridine (299 mg, 1.00 mmol), 2-methoxycarbonylphenylboronic acid (189 mg, 1.05 mmol), palladium(II) acetate (9 mg, 0.04 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (33 mg, 0.08 mmol), and potassium carbonate (414 mg, 3.00 mmol) were dissolved in dioxane/H2O (2.0 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 1 (6 mg, 7% yield) as a solid. LC-MS (M+H=275, obsd.=275). 1H NMR (400 MHz, d6-DMSO): δ 12.22 (s, 1H), 9.11 (d, 1H), 8.64 (d, 1H), 8.61 (d, 1H), 8.33 (d, 1H), 7.91 (t, 1H), 7.73 (t, 1H).

Provenance & Evidence