2-Methoxybenzylamine → 9-(4-Methoxy-benzylamino)-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

9-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.17 mmol), 2-methoxy-benzylamine (36 mg, 0.26 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (7 mg, 0.02 mmol), and sodium tert-butoxide (50 mg, 0.52 mmol) were suspended in dioxane (1 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a filter membrane, and purified via prep-LC-MS. 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 33 (10 mg, 16% yield) as a yellow solid. LC-MS (M+H=332, obsd.=332). 1H NMR (400 MHz, d6-DMSO): δ 11.48 (s, 1H), 8.53 (dd, 1H), 8.42 (dd, 1H), 7.98 (d, 1H), 7.39 (d, 1H), 7.32 (dd, 1H), 7.25 (m, 2H), 7.03 (d, 1H), 6.91 (m, 2H), 4.43 (s, 2H), 3.88 (s, 3H).

Provenance & Evidence