[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.[C:15]1([N:21]2[C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=[N:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11](=[O:14])[N:12]([C:25]2[N:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:22]=[CH:23][CH:24]=2)[CH:13]=15-(2-Fluorophenyl)pyridin-2(1H)-one (0.0281 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0802 g) and copper(II) acetate (0.0539 g) were suspended in pyridine (1.48 mL), and the suspension was stirred at room temperature for 12 hr and further at 90° C. for 6 hr. To the reaction mixture were added 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0802 g) and copper(II) acetate (0.0539 g) at room temperature, and the mixture was heated under reflux for 1.5 days. The reaction mixture was cooled to room temperature, purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (0.0007 g).
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