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

Participants

Reaction Conditions

Reaction Steps

2-Amino-3-bromopyridine (173 mg, 1.00 mmol), 2-methoxycarbonyl-phenylboronic acid (225 mg, 1.25 mmol), Pd(OAc)2 (9 mg, 0.04 mmol), S-Phos (33 mg, 0.08 mmol), and K2CO3 (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 (75 mg, 38% yield) as a solid. LC-MS (M+H=197, obsd.=197). 1H NMR (400 MHz, d6-DMSO): δ 12.08 (s, 1H), 8.83 (d, 1H), 8.55 (d, 1H), 8.49 (dd, 1H), 8.42 (d, 1H), 7.90 (t, 1H), 7.70 (t, 1H), 7.33 (dd, 1H).

Provenance & Evidence