[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[NH2:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:16]=[C:15]([CH3:25])[CH:14]=1.C(N(CC)C(C)C)(C)C.O>S(Cl)(Cl)=O.C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:16]=[C:15]([CH3:25])[CH:14]=1)=[O:7]3-Iodo-4-methylbenzoic acid (1.00 g, 3.89 mmol) was dissolved in thionyl chloride (12.5 mL) and was stirred at 80° C. for 1.75 hours, then thionyl chloride was evaporated under reduced pressure. The reaction mixture was dissolved in methylene chloride (10.0 mL) and the solution was added with a solution of 5-amino-3-methyl-1-(p-tolyl)pyrazole (0.728 g, 3.89 mmol) and N,N-diisopropylethylamine (0.678 mL, 3.89 mmol) in methylene chloride (10.0 mL), followed by stirring at room temperature overnight. After the reaction mixture was added with water and extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, saturated aqueous ammonium chloride solution and water, followed by drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain 3-iodo-4-methyl-N-[5-methyl-2-(p-tolyl)-2H-pyrazol-3-yl]benzamide (1.44 g, 86%).
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