[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[NH:4][N:3]=1.[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([CH3:12])[N:3]=13-bromo-5-chloro-1H-indazole (7.5 g, 32.4 mmol) was dissolved in anhydrous DMF (60 mL) then cooled to 0° C. With vigorous stirring, cesium carbonate (13.36 g, 41 mmol) was added in one portion followed by dropwise addition of iodomethane (2.55 mL, 41 mmol). The reaction was then stirred at 0° C. for 1 hour. The reaction was diluted with distilled water (80 mL), and extracted with EtOAc (3×60 mL). The organic extracts were washed with brine (2×), dried over Na2SO4, and purified by column chromatography (gradient 0 to 15% EtOAc/hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=1.8 Hz, 1H), 7.38 (dd, J=8.9, 1.9 Hz, 1H), 7.30 (d, J=8.9 Hz, 1H), 4.04 (s, 3H).
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