Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=2)[C:8]#[N:9])=[CH:20][CH:19]=1To a suspension of 2-chloro-4-pyridinecarbonitrile (0.50 g, 3.61 mmol), Cs2CO3 (1.70 g, 7.22 mmol) and 4-(trifluoromethyl)phenylboronic acid (0.82 g, 3.61 mmol) in dioxane (18 mL) was added palladium acetate (0.02 g, 0.07 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.07 g, 0.14 mmol). The reaction vessel was sealed and heated to 100° C. for 4 hours and cooled to rt. The reaction mixture was filtered through a pad of celite, concentrated and purified by FCC (0%-100% EtOAc in hexane) to provide the desired product (0.69 g, 78%). MS (ESI): mass calcd. for C13H7F3N2, 248.2; m/z found 249.1 [M+H]+. 1H NMR (400 MHz, DMSO) δ 9.00-8.92 (m, 1H), 8.63-8.57 (m, 1H), 8.38 (d, J=8.1, 2H), 7.94-7.85 (m, 3H).
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