[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:12]([OH:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:9]=1)=[O:7])[CH3:4].[CH2:28](Br)[CH:29]=[CH2:30].C(OCC)(=O)C>CS(C)=O>[CH2:3]([O:5][C:6]([C:8]1[C:12]([O:13][CH2:30][CH:29]=[CH2:28])=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:9]=1)=[O:7])[CH3:4]To a slurry of sodium hydride (39 mg of 60% in oil) in DMSO (2.4 ml) was added 5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid ethyl ester I-1d (300 mg, 0.8 mmol) and the mixture was agitated for 45 minutes. Allyl bromide (0.1 ml, 1.2 mmol) was added and stirring was continued for 4.5 hours. The reaction solution was diluted into ethyl acetate, washed with water (2×), brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound (I-1e) as an orange oil, 340 mg. This material was taken onto the next step without further purification.
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