C[Si]([C:5]#[N:6])(C)C.[C:7]1([C:13]2[C:24]([CH2:25]O)=[C:16]3[C:17]4[CH:23]=[CH:22][O:21][C:18]=4[CH:19]=[CH:20][N:15]3[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClCCl.C(=O)([O-])O.[Na+]>[C:7]1([C:13]2[C:24]([CH2:25][C:5]#[N:6])=[C:16]3[C:17]4[CH:23]=[CH:22][O:21][C:18]=4[CH:19]=[CH:20][N:15]3[N:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1To a solution of boron trifluoride diethyl ether complex (460 μL, 3.63 mmol) and trimethylsilyl cyanide (645 μL, 4.84 mmol) in dichloromethane (12 mL) was added a solution of (2-phenylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol (320 mg, 1.21 mmol) in dichloromethane (12 mL) under ice-cooling and an argon atmosphere, and the mixture was stirred for 2 hr. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50) to give the title compound (240 mg, yield 73%).
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