Potassium Carbonate → HCID 59631873, compound

HRID 2369072Notes

Reaction equation

HRID 2369072 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[N:9]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[O:19][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:11][C:10]([C:20]([F:23])([F:21])[F:22])=[N:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 59631919HCID 59631919, compound

Product 1

HCID 59631873HCID 59631873, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenol (229 mg, 0.68 mmol) and K2CO3 (179 mg, 1.3 mmol) in acetonitrile (3.0 mL) was added methyl bromoacetate (85 μL, 0.90 mmol). The suspension was stirred at ambient temperature for 16 hours at which time HPLC analysis showed conversion to a product with a slightly longer retention time. The reaction suspension was filtered through a plug of Celite that was then washed thoroughly with EtOAc. The filtrate was concentrated to afford a pale yellow oil. This material was further purified by flash column chromatography eluting with a gradient from 0% to 28% EtOAc/hexane to afford methyl 2-(3-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenoxy)acetate (158 mg, 57% yield) as an oil. MS(ES): 411 [M+H]+.

Workup

  1. filtrationThe reaction suspension was filtered through a plug of Celite that
  2. washwas then washed thoroughly with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customto afford a pale yellow oil
  5. customThis material was further purified by flash column chromatography
  6. washeluting with a gradient from 0% to 28% EtOAc/hexane

Sources & evidence

ORD record
ord-a5bd6d8d21014d3db798d2b0904fccbf
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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