Dimethylformamide → 1-(4-Cyano-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 3-aminophenol (43 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 132 (3 mg, 8% yield) as a solid. LC-MS (M+H=304, obsd.=304). 1H NMR (400 MHz, d6-DMSO): δ 12.09 (s, 1H), 9.04 (d, 1H), 8.42 (dd, 1H), 8.28 (d, 1H), 7.78 (dt, 1H), 7.69 (t, 1H), 7.13 (t, 1H), 6.63 (d, 1H), 6.52 (dd, 1H), 6.39 (m, 2H), 5.54 (s, 2H).

Provenance & Evidence