[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Br:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1/[CH:20]=[CH:21]/[C:22]#[N:23]>CS(C)=O.C(OCC)(=O)C>[Br:9][C:10]1[CH:18]=[CH:17][C:16]2[C:12](=[CH:13][N:14]([CH3:19])[N:15]=2)[C:11]=1[CH:20]1[CH2:4][CH:21]1[C:22]#[N:23]
To a suspension of sodium hydride (19.6 mg, 0.490 mmol) in dimethyl sulfoxide (2 mL) was added trimethylsulfoxonium iodide (117 mg, 0.531 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. Thereto was added a solution of (2E)-3-(5-bromo-2-methyl-2H-indazol-4-yl)acrylonitrile (107 mg, 0.408 mmol) in dimethyl sulfoxide (2 mL), and the mixture was stirred for 48 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0) to give the title compound (50.0 mg, yield 44%).
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