Toluene → Ethyl 5-(4-chlorophenyl)-4-cyclopropyl-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate

HRID 254808Notes

Reaction equation

HRID 254808 reaction equation
Br[C:2]1[C:3]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:33]1([CH3:39])C=CC=C[CH:34]=1>>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[N:5]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:4]=[C:3]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:2]=2[CH:39]2[CH2:33][CH2:34]2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 10939684Ethyl 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 25149343Ethyl 5-(4-chlorophenyl)-4-cyclopropyl-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylateYield 44%

Procedure

To a solution of ethyl 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate (68) (500 mg, 1.1 mmol) in aqueous toluene, tetrakis(triphenylphsophine)palladium (122 mg, 0.11 mmol) and potassium carbonate (510 mg, 3.9 mmol) were added. The reaction mixture was placed under microwave irradiation with the temperature set to 140° C. The resulting solution was filtered with syringe filter, and then solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography to obtain the title compound (283 mg, 44%) as white solid.

Workup

  1. customThe reaction mixture was placed under microwave irradiation with the temperature
  2. customset to 140° C
  3. filtrationThe resulting solution was filtered with syringe
  4. filtrationfilter
  5. customsolvent was evaporated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-8b2322a95d644710aae56036fb10e63c
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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