Pyrazole → HCID 61532030, compound

HRID 500188Notes

Reaction equation

HRID 500188 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([F:10])[CH:3]=1.[NH:11]1[CH:15]=[CH:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 61532030HCID 61532030, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromo-1-(bromomethyl)-2-fluorobenzene (0.268 g, 1.0 mmol), 1H-pyrazole (0.0681 g, 1.0 mmol) and cesium carbonate (0.489 g, 1.5 mmol) in N,N-dimethylformamide (1.0 mL) was heated at 90° C. for 3 h. After cooling to RT, the mixture was diluted with EtOAc, and filtered. The filtrate was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue (210 mg, 82.3%) was directly used in next step without further purification. LCMS: (M+H)=256.9/254.9.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationfiltered
  3. washThe filtrate was washed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue (210 mg, 82.3%) was directly used in next step without further purification

Sources & evidence

ORD record
ord-1b1ea0126d0c462a950cd6a445a5cf86
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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