Benzamide, N-(4-aminophenyl)- → 1-(4-tert-Butyl-phenylamino)-5H-benzo[c][1,8]naphthyridin-6-one

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1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4′-aminobenzanilide (92 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 (83 mg, 0.87 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction solution was concentrated, diluted with MeOH/2M HCl/ether, and filtered. The crude product was purified directly via prep-LC-MS. The purified product was converted to the HCl salt via dissolving in MeOH, addition of 2M HCl/ether, and concentration on the Genevac to provide 119 (22 mg, 23% yield) as a dark solid. LC-MS (M+H=407, obsd.=407). 1H NMR (400 MHz, d6-DMSO): δ 10.33 (s, 1H), 9.52 (s, 1H), 8.78 (d, 1H), 8.36 (d, 1H), 8.09 (d, 1H), 7.96 (d, 2H), 7.81 (d, 2H), 7.55 (m, 5H), 7.26 (d, 2H), 6.93 (d, 1H).

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