Aniline → HCID 58168332, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), aniline (40 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (10 mg, 0.02 mmol), and sodium tert-butoxide (63 mg, 0.65 mmol) were suspended in dioxane (2 mL), 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 11 (39 mg, 63% yield) as a white solid. LC-MS (M+H=288, obsd.=288). 1H NMR (400 MHz, d6-DMSO): δ 11.94 (s, 1H), 8.45 (d, 1H), 8.41 (d, 1H), 8.32 (m, 2H), 7.87 (dt, 1H), 7.69 (dt, 1H), 7.27 (dd, 2H), 7.09 (dd, 2H), 6.82 (t, 1H).

Provenance & Evidence