[CH2:1]([O:3][C:4]([C:6]1[C:10](C=O)=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]([C:20]2C=[CH:24][CH:23]=[CH:22][C:21]=2Cl)[N:7]=1)=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:35])C=1.C(OCC)C.C(N(CC)CC)C.Cl[CH2:51][Cl:52]>CO>[CH2:1]([O:3][C:4]([C:6]1[C:10]([OH:35])=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:51]=2[Cl:52])[N:7]=1)=[O:5])[CH3:2]To a stirred solution of 5-(4-chlorophenyl)-1-(2-chlorophenyl)4-formyl-1H-pyrazole-3-carboxylic acid ethyl ester I-1c (2.2 g, 5.6 mmol) in dichloromethane (22 ml) was added m-chloroperbenzoic acid (2.9 g (50% purity), 8.4 mmol) and the resulting slurry was stirred for 6 hours. The mixture was diluted into ethyl ether, washed with half-saturated aqueous sodium bicarbonate, water, brine, dried (Na2SO4) and concentrated in vacuo to afford a yellow solid, 3.5 g. To a slurry of this material in methanol (20 ml), was added triethylamine (1 ml) to produce a solution. After 45 minutes, the reaction was concentrated in vacuo to afford a yellow solid. This material was purified by silica gel chromatograpy (Combiflash instrument, 120 g silica gel column, 5–25% gradient of ethyl acetate/hexanes to afford the title compound (I-1d) as a yellow solid, 1.5 g.
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