[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[C:5]2I.[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:22]1[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=1To a 500 ml round bottom flask equipped with a magnetic stir bar was added tert-butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate (6.00 g, 14.2 mmol), followed by the additions of 4-pyridineboronic acid (1.92 g, 15.6 mmol), PdCl2(dppf) (1.16 g, 1.4 mmol) and K3PO4 (9.03 g, 42.5 mmol). The mixture was dissolved in a mixture of 160 ml of dioxane and 40 ml of H2O and stirred overnight at 80° C. Upon completion, the reaction mixture was filtered through celite and washed with water (3×100 ml). The organic phase was then dried over anhydrous MgSO4, filtered and concentrated to dryness to give a crude product. The crude product was column purified to give 5-bromo-3-(pyridin-4-yl)-1H-indazole (2.74 g) as a de-BOc product.
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