[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:17]1[C:25]2[C:21](=[CH:22][N:23]([CH3:26])[N:24]=2)[CH:20]=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:26][N:23]1[CH:22]=[C:21]2[C:25]([C:17]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:18][C:19]([N+:27]([O-:29])=[O:28])=[CH:20]2)=[N:24]1Phenylboronic acid (244 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1, 40 mg), dioxane (4 mL), a 2 M aqueous sodium carbonate solution (1 mL), and the reaction solution were added to 7-bromo-2-methyl-5-nitro-2H-indazole obtained in the above-described Step 1 (256 mg). The reaction solution was allowed to react in a microwave reactor at 130° C. for 1 hour. The solvent was evaporated under vacuum, and the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 2-methyl-5-nitro-7-phenyl-2H-indazole.
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