P-Anisidine → 8,9-dimethoxy-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

9-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 4-methoxy-aniline (24 mg, 0.20 mmol), palladium(II) acetate (1 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5 mg, 0.015 mmol), and sodium tert-butoxide (38 mg, 0.39 mmol) were suspended in dioxane (1 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. The recovered product was converted to the HCl salt via suspending in CH2Cl2, addition of 2 M HCl/ether, filtering the resulting precipitate, and washing with CH2Cl2 to provide 28 (20 mg, 43% yield) as a yellow solid. LC-MS (M+H=318, obsd.=318). 1H NMR (400 MHz, d6-DMSO): δ 11.60 (s, 1H), 8.44 (dd, 1H), 8.39 (dd, 1H), 8.09 (d, 1H), 7.68 (d, 1H), 7.23 (m, 3H), 7.14 (dd, 1H), 6.97 (m, 2H), 3.77 (s, 3H).

Provenance & Evidence