[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:15]1[N:20]=[C:19]([CH3:21])[C:18]([O:22][CH3:23])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O.C(O)C.O>[CH3:23][O:22][C:18]1[CH:17]=[CH:16][C:15]([C:6]2[CH:7]=[N:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[N:20][C:19]=1[CH3:21]A 20 mL microwave vial was charged with 6-(trifluoromethyl)pyridin-3-ylboronic acid (666 mg, 3.49 mmol), 6-chloro-3-methoxy-2-methylpyridine (500 mg, 3.17 mmol), bis(triphenylphosphine)palladium(II) chloride (111 mg, 0.159 mmol), and K2CO3 (877 mg, 6.35 mmol), followed by the addition of DME (9.0 mL), water (3.86 mL) and ethanol (2.57 mL). The mixture was heated on the microwave at 120° C. for 10 minutes. To the reaction mixture was added 200 mL EtOAc, and washed with 200 mL water and 200 mL brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on a Grace Reveleris 40 g column, eluted with 0-40% EtOAc in Hexanes (25 mL/min) to provide the title compound (1.583 g, 5.90 mmol, 62.0% yield) as a white solid. MS (ESI+) m/z 269.1 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 9.37 (d, J=1.8, 1H), 8.64 (dd, J=8.3, 1.9, 1H), 8.03 (d, J=8.6, 1H), 7.97 (d, J=8.3, 1H), 7.50 (d, J=8.6, 1H), 3.90 (s, 3H), 2.47 (s, 3H).
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