[Br:1][C:2]1[C:3]([O:10][CH:11]([F:13])[F:12])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.BrC1[C:16](OC(F)F)=[N:17][CH:18]=C(C)C=1.BrN1C(=O)CCC1=O.[N:34](C(C)(C)C#N)=[N:35]C(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.O>[N:34]1([CH2:8][C:6]2[CH:7]=[C:2]([Br:1])[C:3]([O:10][CH:11]([F:13])[F:12])=[N:4][CH:5]=2)[CH:18]=[N:17][CH:16]=[N:35]13-Bromo-5-(bromomethyl)-2-(difluoromethoxy)pyridine. To a solution of 3-bromo-2-(difluoromethoxy)-5-methylpyridine (0.50 g, 2.1 mmol) in carbon tetrachloride (13 mL), was added 1-bromopyrrolidine-2,5-dione (0.521 g, 2.93 mmol), and azobisisobutyronitrile (44 mg, 0.26 mmol). The reaction mixture was stirred at 80° C. for 8 h. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 10-90%, EtOAc/hexanes) afforded the title compound (400 mg, 60%). [M+H]=317.88.
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