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

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

Reactant 3

HCID 1140Toluene

HCID 11430Potassium Carbonate

HCID 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.