Water → HCID 68156695, compound
Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.F[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([CH3:19])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:19][C:13]1[CH:12]=[C:11]([N:5]2[CH:4]=[C:3]([C:2]([F:9])([F:8])[F:1])[CH:7]=[N:6]2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-(trifluoromethyl)-1H-pyrazole (1.0 g, 7.0 mmol) and 4-fluoro-2-methylbenzonitrile (1.16 g, 8.50 mmol) in acetonitrile (8 mL) was slowly added potassium carbonate (1.96 g, 14.2 mmol) at room temperature. The reaction was heated to 80° C. and stirred overnight. The reaction was cooled to room temperature and poured into water. The layers were separated and the aqueous was extracted with ethyl acetate (3×15 mL). The combined organics were washed with water, dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave 2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)benzonitrile (710 mg, 40%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.26 (s, 1H), 7.94 (s, 1H), 7.72-7.74 (m, 2H), 7.61-7.64 (m, 1H), 2.64 (s, 3H).
Workup
- customat room temperature
- temperatureThe reaction was cooled to room temperature
- customThe layers were separated
- extractionthe aqueous was extracted with ethyl acetate (3×15 mL)
- washThe combined organics were washed with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash column chromatography
Sources & evidence
- ORD record
- ord-19e72afdadc54ebf9cc4ac0f76d0e125
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859591B2
Reaction notes
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