[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([CH2:13]O)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.S(Cl)(Cl)=O.O.[C-:20]#[N:21].[K+]>C(Cl)Cl.O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[CH:1]1([N:4]2[C:8]([C:9]([F:12])([F:11])[F:10])=[C:7]([CH2:13][C:20]#[N:21])[CH:6]=[N:5]2)[CH2:3][CH2:2]1
A solution of (1-cyclopropyl-5-trifluoromethyl-1H-pyrazol-4-yl)-methanol (Preparation 97, 1.2 g, 5.82 mmol) in DCM (15 mL) was cooled to 0° C. and thionyl chloride (0.85 mL, 11.7 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours and diluted with DCM. The organic layer was washed with water, brine and dried (Na2SO4) and evaporated in vacuo. The crude residue obtained was dissolved in dioxane (25 mL) and water (25 mL) and tetrabutyl ammonium bromide (1.38 g, 4.28 mmol) was added. The reaction mixture was stirred for 10 minutes followed by the addition of KCN (1.28 g, 19.82 mmol) and resultant mixture was stirred for a further 16 hours at room temperature. The mixture was diluted with EtOAc (50 mL) and washed with water (1×10 mL), brine (1×10 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by silica gel column chromatography eluting with Hexane:EtOAc 10:90 to afford the title compound as light yellow solid (56%, 700 mg).
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