Acetonitrile → 2-(4-Fluoro-1H-pyrazol-1-yl)propanenitrile
Reaction equation
[F:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Cl[CH:8]([CH3:11])[C:9]#[N:10].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[F:1][C:2]1[CH:3]=[N:4][N:5]([CH:8]([CH3:11])[C:9]#[N:10])[CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
4-Fluoro-1H-pyrazole (300 mg, 3.49 mmol), 2-chloropropanenitrile (374 mg, 4.18 mmol), cesium carbonate (1.84 g, 5.23 mmol) and anhydrous acetonitrile (5.0 mL) were added into a round bottom flask. The reaction mixture was heated to 100° C. for 2 h. Water was added and the mixture was extracted with ether (100 mL×3). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (0-50% ethyl acetate in heptanes) to afford 2-(4-Fluoro-1H-pyrazol-1-yl)propanenitrile (398 mg, 82%). MS (EI+) (M+) 139, GCMS retention time: 0.78 min (Method O).
Workup
- extractionthe mixture was extracted with ether (100 mL×3)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude material was purified via flash chromatography (0-50% ethyl acetate in heptanes)
Sources & evidence
- ORD record
- ord-0ac5c7c7583f4d21bc6186734aea5aa7
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296745B2
Reaction notes
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