Potassium Carbonate → HCID 59240173, compound

HRID 1673017Notes

Reaction equation

HRID 1673017 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:10]=[C:9]([OH:19])[CH:8]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>CN(C=O)C>[CH3:31][O:30][C:28](=[O:29])[CH2:27][O:19][C:9]1[CH:8]=[C:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178515507HCID 178515507, compound

Product 1

HCID 59240173HCID 59240173, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(5-bromo-thiophene-2-yl)-1-(2-chloro-phenyl)-1H-pyrazole-3-ol (2.21 g, 6.21 mmol) in anhydrous DMF was added K2CO3 (1.72 g, 12.43 mmol) and methyl bromoacetate (1.2 mL, 12.43 mmol). The reaction mixture was heated at 80° C. under nitrogen atmosphere overnight. Evaporate the solvent and the residue was dissolved in DCM and it was passed through a short pad of celite. The solvent was concentrated and the crude product was purified by flash column chromatography (20% ethyl acetate in hexane), resulting in the product of [5-(5-bromo-thiophen-2-yl)-1-(2-chloro-phenyl)-1H-pyrazol-3-yloxy]-acetic acid methyl ester (2.36 g, 89% yield).

Workup

  1. customEvaporate the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. concentrationThe solvent was concentrated
  4. customthe crude product was purified by flash column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-44228d72abc544dbae6ef58a8dc689fd
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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