Aniline → HCID 58167963, compound

Participants

Reaction Conditions

Reaction Steps

9-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), aniline (30 mg, 0.33 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8 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 added directly to a Biotage column. The crude product was purified via Biotage silica-gel chromatography eluting with a gradient of 0 to 10% MeOH in CH2Cl2 to provide 23 (20 mg, 32% yield) as a tan solid. LC-MS (M+H=288, obsd.=288). 1H NMR (400 MHz, d6-DMSO): δ 11.69 (s, 1H), 8.95 (s, 1H), 8.47 (m, 2H), 8.15 (d, 1H), 7.86 (d, 1H), 7.386 (m, 2H), 7.29 (m, 3H), 7.04 (t, 1H).

Provenance & Evidence