Potassium Carbonate → ethyl 1-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate

HRID 2209195Notes

Reaction equation

HRID 2209195 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)=[O:4].[NH:15]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:16]2[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:19]=[N:15]2)[CH:10]=[CH:9][C:8]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-oneHCID 178469268HCID 178469268, compound

Product 1

HCID 117843714ethyl 1-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 2-bromo-1-(3,4-dimethoxyphenyl)ethanone (1.95 g, 7.53 mmol) and ethyl 1H-pyrazole-3-carboxylate (1.22 g, 8.72 mmol) in acetone (36 mL) at room temperature was added potassium carbonate (1.28 g, 9.23 mmol). Mixture stirred vigorously overnight and then was concentrated under reduced pressure. Resulting residue was taken up in ethyl acetate and washed with 4:1 water/brine. Layers were separated and aqueous was extracted with ethyl acetate. Combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. Resulting residue was purified by silica gel column chromatography (10-60% ethyl acetate in hexanes) to yield ethyl 1-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate 5.01.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washwashed with 4:1 water/brine
  3. customLayers were separated
  4. extractionaqueous was extracted with ethyl acetate
  5. dry with materialCombined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customResulting residue was purified by silica gel column chromatography (10-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5e0338529d884e8c8b07dbc684c25977
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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