Water → HCID 58081217, compound

HRID 928407Notes

Reaction equation

HRID 928407 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.Br[C:12]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[CH:14][C:13]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:9]([O:8][C:6]([C:4]1[CH:5]=[N:1][N:2]([CH2:21][C:13]2[CH:12]=[CH:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=2)[CH:3]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 821303-Bromo-4-methylbenzoic acidHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 58081217HCID 58081217, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl pyrazole-4-carboxylate (500 mg, 3.57 mmol) and bromo-para-toluic acid (767 mg, 3.57 mmol) in acetone (10 ml) was added potassium carbonate (2.465 g, 17.84 mmol). The suspension was stirred at 50° C. overnight. Water was added to the reaction, and the aqueous phase was washed with ethyl acetate. The pH of the aqueous phase was acidified with 1M hydrochloric acid, and the product was extracted with ethyl acetate. Organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound. HPLC (method G) Rt=1.642 min; UPLC (method F) Rt=0.69 min, [M+H]+275.3 [M−H]− 273.3.

Workup

  1. washthe aqueous phase was washed with ethyl acetate
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7d7c1d2530144cbdbbd368f20a8b0ffd
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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