I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[N:16]=2)[N:3]=1.[CH:23]([B-](F)(F)F)=[CH2:24].[K+].C(N(CC)CC)C>CC(O)C.C1COCC1>[CH3:22][O:21][C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:23]=[CH2:24])=[N:3]2)[CH:20]=[CH:19][CH:18]=1To 3-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazole (2.65 g, 6.46 mmol) in IPA/THF (40 mL/10 mL) was added potassium vinyltrifluoroborate (1.30 g, 9.69 mmol), triethylamine (1.31 g, 12.9 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.264 g, 0.323 mmol). The reaction mixture was heated to reflux and stirred for 16 hours. The reaction mixture was cooled to ambient temperature and concentrated to remove solvent. The residue was dissolved with EtOAc (100 mL) and washed with saturated NH4Cl, H2O and brine. The solution was dried (Na2SO4) and concentrated to provide the desired product (1.89 g).
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