[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[CH3:12].[CH3:13][C:14]1[C:18]([CH3:19])=[C:17]([CH3:20])[NH:16][N:15]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:15]2[C:14]([CH3:13])=[C:18]([CH3:19])[C:17]([CH3:20])=[N:16]2)=[CH:5][C:4]=1[CH3:12]A mixture of 4-methoxy-3-methyl-phenylboronic acid 10 g, 3,4,5-trimethyl-1H-pyrazole (described in Reference Preparation example 49) 7.3 g, copper(II) acetate 18.4 g, pyridine 10.0 g, molecular sieves 4 A 20.0 g and acetonitrile 300 ml was stirred with heating under reflux for thirty hours. The reaction mixture was filtered through Celite and was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(4-methoxy-3-methyl-phenyl)-3,4,5-trimethyl-1H-pyrazole 7.3 g.
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