Br[C:2]1[CH:7]=[C:6]([NH:8]C(=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]=1.[Cl:16][C:17]1[C:18]([F:27])=[CH:19][C:20]([F:26])=[C:21](B(O)O)[CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].FC(F)(F)C(O)=O>O1CCOCC1.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:16][C:17]1[C:18]([F:27])=[CH:19][C:20]([F:26])=[C:21]([C:2]2[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=2)[CH:22]=1tert-Butyl 2-bromopyridin-4-ylcarbamate (258 mg, 0.945 mmol), 5-chloro-2,4-difluorophenylboronic acid (236 mg, 1.228 mmol) and bis(triphenylphosphine) palladium chloride (133 mg, 0.189 mmol) were combined in dioxane (5 mL) and saturated Na2CO3 (0.472 ml, 0.945 mmol). The reaction mixture was heated at 90° C. in an oil bath. After 12 hours, the reaction mixture was cooled, water (10 mL) was added and the reaction mixture was extracted with EtOAc (100 mL, 2×). The organic layers were combined, washed with brine, dried over Na2SO4, filtered, and concentrated to give a residue. The residue was dissolved in dichloromethane (4 mL) and trifluoroacetic acid was added (4 mL). The reaction was stirred at room temperature for 20 minutes then the solvent was removed on a rotavap and the residue was further dried under high vacuum overnight. This residue was purified by NH column chromatography, eluted with EtOAc in Hexanes (0-100%) to give the title compound (49 mg) as white solid. ESI-MS: m/z 242.0 (M+H).
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