A mixture of 7-chloro-3-(5-fluoro-4-methylpyridin-3-yl)-2,6-naphthyridine 2-oxide (150 mg, 0.52 mmol), tert-butyl carbamate (121 mg, 1.04 mmol), 2-(dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl (58 mg, 0.10 mmol), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoeth yl)phenyl]palladium(II) (42 mg, 0.052 mmol), and cesium carbonate (341 mg, 1.04 mmol) in dioxane (2.5 mL) was heated at 100° C. for 8 hours in a vial sealed with a Teflon cap. The reaction mixture was diluted with dichloromethane (50 mL) and methanol (5 mL), filtered over Celite, and concentrated in vacuo to provide a residue that was purified by flash chromatography (12 g, Silica, 0-10% methanol in dichloromethane). Desired fractions were combined and evaporated in vacuo to afford the title compound as a yellow solid (73 mg, 38%). 1H NMR (400 MHz, DMSO) δ 10.16 (s, 1H), 9.14 (s, 1H), 9.08 (s, 1H), 8.62 (s, 1H), 8.39 (s, 1H), 8.21 (s, 1H), 8.16 (s, 1H), 1.52 (s, 9H).
