Ethyl bromoacetate → Ethyl 4-iodo-1H-pyrazole-1-acetate

HRID 1774505Notes

Reaction equation

HRID 1774505 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1)[CH3:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 770224-Iodopyrazole

Product 1

HCID 46738002Ethyl 4-iodo-1H-pyrazole-1-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Iodo-1H-pyrazole (2 g, 10.3 mmol), ethyl bromoacetate (2.3 mL, 20.6 mmol) and cesium carbonate (5 g, 15.5 mmol) were combined in DMF (20 mL). After stirring at room temperature for 30 minutes the reaction was diluted with EtOAc/hexanes (1:1) and washed with H2O/brine, with back-extraction. The organic layer was dried over MgSO4, concentrated and filtered via silica gel chromatography (0-20% EtOAc in hexanes) to give the title compound.

Workup

  1. washwashed with H2O/brine, with back-extraction
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. filtrationfiltered via silica gel chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-aea25c8523ee4d4ab108f25fa5bd7ad9
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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