3-Fluoroaniline → 9-(2-Methoxy-phenylamino)-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), 3-fluoro-aniline (22 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 30 (17 mg, 38% yield) as a yellow solid. LC-MS (M+H=306, obsd.=306). 1H NMR (400 MHz, d6-DMSO): δ 11.73 (s, 1H), 8.55 (dd, 1H), 8.47 (dd, 1H), 8.19 (d, 1H), 7.95 (d, 1H), 7.38 (m, 2H), 7.29 (dd, 1H), 7.12 (dd, 1H), 7.07 (m, 1H), 6.80 (dt, 1H).

Provenance & Evidence