[N+:1]([C:4]1[C:5]([C:9]([O-:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=C[CH:23]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N+:1]([C:4]1[C:5]([C:9]([O:11][CH3:23])=[O:10])=[N:6][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)([O-:3])=[O:2]To a solution of 4-nitro-1H-pyrazole-3-carboxylate (1.0 g, 5.84 mmol) in methylene chloride (20 mL) were added phenylboric acid (1.43 g, 11.7 mmol), copper(II) acetate (1.60 g, 8.76 mmol) and pyridine (2 mL, 23.4 mmol), and the mixture was stirred overnight at room temperature under an air atmosphere. After removal of the insolubles by filtration, the filtrate was washed with water (twice) and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title compound (1.21 g, 83.5%).
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