2-Methylbenzylamine → 9-[(Naphthalen-1-ylmethyl)-amino]-5H-benzo[c][1,8]naphthyridin-6-one

Participants

Reaction Conditions

Reaction Steps

9-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 2-methylbenzylamine (53 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (10 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 concentrated, diluted with H2O/EtOAc, and filtered. The precipitate was washed with EtOAc/H2O and purified via prep-LC-MS. The purified product was converted to the HCl salt via dissolving in MeOH, addition of 1 M HCl/ether, and concentration. The HCl salt was triturated in CH2Cl2, filtered, washed with CH2Cl2, and dried under vacuum to provide 45 (25 mg, 33% yield) as a yellow solid. LC-MS (M+H=316, obsd.=316). 1H NMR (400 MHz, d6-DMSO): δ 11.50 (s, 1H), 8.59 (dd, 1H), 8.42 (dd, 1H), 8.00 (d, 1H), 7.41 (d, 1H), 7.33 (dd, 1H), 7.22 (m, 4H), 6.98 (dd, 1H), 4.45 (s, 2H), 2.37 (s, 3H).

Provenance & Evidence