[C:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21](OS(C(F)(F)F)(=O)=O)=[CH:20][CH:19]=2)=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]([CH3:12])[C:7]=1[C:8]([F:11])([F:10])[F:9])#[N:2].[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O)#[N:33].C1(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH2:16]([O:15][C:13]([C:5]1[N:6]([CH3:12])[C:7]([C:8]([F:9])([F:10])[F:11])=[C:3]([C:1]#[N:2])[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[C:32]#[N:33])=[CH:20][CH:19]=1)=[O:14])[CH3:17]Prepare the title compound in a manner analogous to the procedure described in Scheme IIIa. For example, place ethyl 4-cyano-1-methyl-5-(trifluoromethyl)-3-{4-[(trifluoromethyl)sulfonyloxy]phenyl}pyrrole-2-carboxylate (11.0 mmol, prepared in example E-277), 2-cyano-phenyl boronic acid (1.5 mmol), palladium (II) acetate (0.12 mmol), triphenylphosphate (0.24 mmol), and tribasic potassium phosphate (3.6 mmol) in a round bottom flask and add dioxane. Heat reaction to reflux for 18 hours, remove the heat and wash with water while extracting with ethyl acetate. Dry organics with sodium sulfate, filter, and concentrate in vacuo. Purify the residue via radial chromatography eluting with methylene chloride, ethyl acetate and hexane to provide the title compound.
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