Pyrazole → methyl 4-cyano-3-(1H-pyrazol-1-yl)benzoate

HRID 587850Notes

Reaction equation

HRID 587850 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1F)#[N:2].[NH:14]1[CH:18]=[CH:17][CH:16]=[N:15]1.[H-].[Na+]>CN(C)C=O.O>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N:14]1[CH:18]=[CH:17][CH:16]=[N:15]1)#[N:2]

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 17965941Methyl 4-cyano-3-fluorobenzoate

Product 1

HCID 66973486methyl 4-cyano-3-(1H-pyrazol-1-yl)benzoateYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 4-cyano-3-fluorobenzoate (0.30 g) and 1H-pyrazole (0.14 g) were dissolved in N,N-dimethylformamide (10 ml). To the reaction solution, sodium hydride (0.10 g) was added under ice cooling while stirring the mixture, and the mixture was stirred for 30 min. After increasing the temperature to room temperature, the solution was further stirred for 2 hours. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with water, and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product, which was then purified by column chromatography to give methyl 4-cyano-3-(1H-pyrazol-1-yl)benzoate (0.28 g, yield 73%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe solution was further stirred for 2 hours
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was removed by filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-47ef1b4329fc4a068081e8234b3aabf4
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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