Cesium carbonate → ethyl 1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-4-carboxylate

HRID 1026751Notes

Reaction equation

HRID 1026751 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[F:11][C:12]([F:22])([F:21])[O:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I>[F:11][C:12]([F:21])([F:22])[O:13][C:14]1[CH:19]=[CH:18][C:17]([N:1]2[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 27772941-Iodo-4-(trifluoromethoxy)benzene

Product 1

HCID 44818853ethyl 1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-4-carboxylateYield 9.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 4-pyrazolecarboxylate (500 mg), 4-(trifluoromethoxy)iodobenzene (1.00 g), trans-1,2-bis(methylamino)cyclohexane (100 mg), copper iodide (70 mg) and cesium carbonate (1.7 g) in dioxane (5.0 mL) was stirred while heating at 100° C. for 5 hr. The reaction mixture was filtered through Celite and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-80:20) to afford ethyl 1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-4-carboxylate (100 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. distillationthe solvent was then distilled off under reduced pressure
  3. customThe resulting residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=98:2-80:20)

Sources & evidence

ORD record
ord-dcfc75416d304d979c185c5d78ac54a8
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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