[NH2:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[CH:12][C:13](C(OC)=O)=[C:14](B(O)O)[CH:15]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[C:52](=[O:55])([O-])[O-].[K+].[K+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:9][C:10]1[CH:15]=[CH:14][C:13]2[C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[NH:1][C:52](=[O:55])[C:12]=2[CH:11]=12-Amino-3-bromopyridine (87 mg, 0.50 mmol), 5-fluoro-2-methoxycarbonylphenylboronic acid (149 mg, 0.75 mmol), palladium(II) acetate (5 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (16 mg, 0.04 mmol), and potassium carbonate (207 mg, 1.50 mmol) were dissolved in dioxane/H2O (1.65 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 3 (35 mg, 33% yield) as a solid. LC-MS (M+H=215, obsd.=215). 1H NMR (400 MHz, d6-DMSO): δ 12.12 (s, 1H), 8.84 (d, 1H), 8.53 (d, 1H), 8.43 (d, 1H), 8.38 (dd, 1H), 7.53 (t, 1H), 7.33 (dd, 1H).
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