Pyrazole → HCID 61532030, compound

HRID 1257844Notes

Reaction equation

HRID 1257844 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-beba9df95fb34e52be0c552a66d50b22
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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