[F:1][C:2]1[C:3]([C:9](N(OC)C)=[O:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH4+].[Cl-]>C1COCC1>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:9]([C:3]2[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][N:4]=2)=[O:10])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1To a stirred solution of 3,5-difluoro-N-methoxy-N-methylpyridine-2-carboxamide (2.5 g) in THF (50 mL) was added [4-(benzyloxy)phenyl](bromo)magnesium (1 M solution in THF, 12.3 mL) at −78° C. The mixture was stirred at −78° C. for 3 h, treated with saturated NH4Cl aqueous solution and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane). The product was crystallized from AcOEt/hexane to give the title compound (2.3 g).
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