I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:11]=[N:12][NH:13][CH:14]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH:11]=[C:10]([CH3:9])[CH:14]=[N:13]2)=[CH:3][CH:4]=1A mixture of 1,4-diiodobenzene (4.00 g, 12.1 mmol), 4-methylpyrazole (0.972 g, 12.1 mmol), 8-hydroxyquinoline (0.176 g, 1.21 mmol) and K2CO3 (1.69 g, 12.2 mmol) in DMSO (12 mL) was degassed before being charged with CuI (0.310 g, 1.63 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered. The organic layer was separated, then applied to a silica gel column, which was eluted with hexane, then with 5% EtOAc in hexane to give 1-(4-iodophenyl)-4-methyl-1H-pyrazole (1.70 g).
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