Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[C:5]([Cl:10])[CH:4]=1.[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:10][C:5]1[CH:4]=[C:3]([CH2:2][C:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=2)[C:8]([Cl:9])=[CH:7][N:6]=1To a solution of 4-bromomethyl-2,5-dichloro-pyridine (500 mg, 2.08 mmol) in toluene (10 mL) was added with stirring the [1,1-bis(diphenylphos-phino)ferrocene]dichloropalladium DCM complex (74 mg, 0.101 mmol), B-(3-fluorophenyl)-boronic acid (290 mg, 2.08 mmol) and sodium carbonate (440 mg, 4.15 mmol) in water (2 mL). The resulting mixture was stirred at 80° C. for 3 h, cooled, poured onto water (20 mL), and partitioned between water and ethyl acetate. The organic portions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient) to give the title compound (241 mg, 32%) as white solid. LC-MS (UV peak area, m/z) 70%, 255.0, 257.0 (M+).
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