3-Methoxybenzylamine → 1-(4-Methoxy-benzylamino)-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.22 mmol), 3-methoxybenzylamine (48 mg, 0.35 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (7 mg, 0.02 mmol), and sodium tert-butoxide (67 mg, 0.69 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was concentrated, partitioned between H2O/EtOAc, and filtered. The precipitate was washed with H2O/EtOAc, and suspended in MeOH. 2M HCl/ether was added and the resulting mixture was filtered. The precipitate (Pd salts) was washed with MeOH, and the filtrate was concentrated. The crude product was purified via prep-LC-MS. The purified product was converted to the HCl salt via dissolving in MeOH, addition of 2 M HCl, and evaporation. The resulting precipitate was triturated from CH2Cl2, filtered, and dried under vacuum to provide 97 (10 mg, 16% yield) as a yellow solid. LC-MS (M+H=332, obsd.=332). 1H NMR (400 MHz, d6-DMSO): δ 9.10 (s, 1H), 8.63 (d, 1H), 8.38 (d, 1H), 8.08 (d, 1H), 7.98 (t, 1H), 7.71 (m, 2H), 7.29 (t, 1H), 7.05 (m, 2H), 6.87 (dd, 1H), 6.74 (d, 1H), 4.76 (d, 2H), 3.72 (s, 3H).

Provenance & Evidence