Potassium Carbonate → 3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridineacetonitrile
Reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([CH2:8][C:9]#[N:10])=[N:6][CH:7]=1.[F:12][C:13]([F:20])([F:19])[C:14]1[CH:18]=[CH:17][NH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[Cl:11][C:4]1[C:5]([CH2:8][C:9]#[N:10])=[N:6][CH:7]=[C:2]([N:16]2[CH:17]=[CH:18][C:14]([C:13]([F:20])([F:19])[F:12])=[N:15]2)[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-bromo-3-chloro-2-pyridineacetonitrile (i.e. the product of Step A; 6.0 g, 0.025 mol) in 1,4-dioxane (50 mL) was added 3-(trifluoromethyl)-1H-pyrazole (3.74 g, 0.027 mol), copper(I) iodide (0.49 g, 0.0025 mol), potassium carbonate (13.8 g, 0.1 mol) and trans-N,N′-dimethyl-1,2-cyclohexanediamine (1.42 g, 0.01 mol) under argon atmosphere at room temperature, and the resulting mixture was heated at 100° C. for 16 h. The cooled reaction mixture was diluted with ice water and extracted with dichloromethane (2×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (4:6) to afford the title compound (5.0 g) as a light yellow solid.
Workup
- customThe cooled reaction mixture
- extractionextracted with dichloromethane (2×50 mL)
- dry with materialThe combined organic extracts were dried (Na2SO4)
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography
- washeluting with ethyl acetate-hexane (4:6)
Sources & evidence
- ORD record
- ord-0cffb541ea9847b9afcbca97817fa018
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815772B2
Reaction notes
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