[CH:1]([N:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([C:13]#[N:14])[C:6]1=[O:15])([CH2:3][CH3:4])[CH3:2].[Br:16]N1C(=O)CCC1=O.CN(C)C=O>C(=O)([O-])O.[Na+]>[Br:16][C:9]1[C:8]([O:11][CH3:12])=[C:7]([C:13]#[N:14])[C:6](=[O:15])[N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH:10]=1A mixture of 1-(sec-butyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step A (260 mg), N-bromosuccinimide (269 mg) and N,N-dimethylformamide (3 mL) was stirred at 60° C. for 2 hr 30 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted threetimes with ethyl acetate. The extracts were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (260 mg).
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