[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[N:7]=1.C(=O)([O-])O.[Na+]>CS(C)=O>[F:15][C:14]([F:17])([F:16])[CH2:13][O:12][C:8]1[N:7]=[C:6]([CH2:5][C:1]#[N:2])[CH:11]=[CH:10][CH:9]=1Sodium cyanide (0.823 g, 16.8 mmol) is added to a solution of 2-(chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine (2.0 g, 7.63 mmol, Step-4) in DMSO (38 mL) and stirred at rt for 20 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (60 mL) and extracted with EtOAc (100 mL). The organic layer is washed with water (50 mL×2) and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on amine gel eluting with n-hexane/EtOAc (3:1) to give 1.13 g (69% yield) of the title compound as yellow oil.
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