I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O.C1(C)C=CC=CC=1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([C:2]3[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=3)[CH:17]=[N:16]2)=[CH:11][CH:10]=1Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (600 mg), [1-(4-fluorophenyl)-1H-pyrazol-4-yl]boronic acid (650 mg), tetrakistriphenylphosphine palladium (166 mg), 2 M sodium carbonate aqueous solution (2.9 mL), ethanol (3.0 mL) and toluene (6.0 mL) was stirred at 100° C. for 4 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was concentrated under a reduced pressure, and the residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to ethyl acetate), so as to obtain the title compound (450 mg) in the form of a light yellow solid.
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