Cl[CH2:2][C:3]1[CH:4]=[N:5][N:6]([CH:12]([CH3:14])[CH3:13])[C:7]=1[C:8]([F:11])([F:10])[F:9].[C-:15]#[N:16].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.O.CCOC(C)=O>[CH:12]([N:6]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:3]([CH2:2][C:15]#[N:16])[CH:4]=[N:5]1)([CH3:14])[CH3:13]
Tetrabutyl ammonium bromide (7.95 gm, 24.7 mmol) was added to 4-(chloromethyl)-1-isopropyl-5-(trifluoromethyl)-1H-pyrazole (7 g, 31 mmol) in dioxane (75 mL) and water (75 mL) and the mixture was stirred for 10 min. Potassium cyanide (7.42 g, 114 mmol) was added and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with EtOAc (100 mL) then the organic phase was washed with water (100 mL), brine (100 mL) and dried over sodium sulphate. The filtrate was evaporated in vacuo and purified by column chromatography on silica gel (hexane:EtOAc 90:10) to afford the title compound as a white solid in 100% yield, 7.00 g.
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