Water → HCID 25052028, compound

HRID 1516583Notes

Reaction equation

HRID 1516583 reaction equation
[Br:1][C:2]1[C:3]([C:7]#[N:8])=[N:4][NH:5][CH:6]=1.[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1)[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:9]([O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([N:5]2[CH:6]=[C:2]([Br:1])[C:3]([C:7]#[N:8])=[N:4]2)=[CH:15][CH:14]=1)[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 27356234-Bromo-1H-pyrazole-3-carbonitrile

Product 1

HCID 25052028HCID 25052028, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-bromo-1H-pyrazole-3-carbonitrile (0.52 g), 4-fluoro-benzoic acid ethyl ester (0.56 g) and cesium carbonate (1.5 g) in N,N-dimethylformamide (10 mL) was stirred at 100° C. for 2 hours. After cooling to ambient temperature, this reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The organic layer was through an aminopropyl silica gel, and this filtrate was concentrated under reduced pressure. This obtained residue was washed with a mixed solvent of n-hexane/diethyl ether=5/1 to give the title compound (0.25 g).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthis mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationthis filtrate was concentrated under reduced pressure
  6. washThis obtained residue was washed with a mixed solvent of n-hexane/diethyl ether=5/1

Sources & evidence

ORD record
ord-f9b9616cd604480381cc26d2d31ef02a
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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