2-Fluoroaniline → HCID 69813141, compound

Participants

Reaction Conditions

Reaction Steps

8-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 2-fluoroaniline (48 mg, 0.43 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 diluted with MeOH, filtered through a membrane plug, and purified via prep-LC-MS to provide 17 (25 mg, 38% yield) as a tan solid. LC-MS (M+H=306, obsd.=306). 1H NMR (400 MHz, d6-DMSO): δ 11.92 (s, 1H), 8.66 (dd, 1H), 8.58 (s, 1H), 8.39 (m, 2H), 7.75 (d, 1H), 7.44 (m, 2H), 7.32 (dd, 1H), 7.28 (dd, 1H), 7.21 (dt, 1H), 7.11 (m, 1H).

Provenance & Evidence