[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2.[OH-].[K+].[I:20]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[I:20]To a solution of 5-(3-chlorophenoxy)-1H-indazole (152 mg, 621 μmol) in DMF (2.36 mL) at 25° C. was added potassium hydroxide (105 mg, 1.86 mmol) and iodine (237 mg, 932 μmol). The reaction mixture was stirred at 25° C. for 75 min then quenched with 10% Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (3×), then the combined organics were washed with water and brine (2×), dried over MgSO4 and concentrated to afford a pale yellow oil which was purified by chromatography (silica, 115 g, 50 μm from Analogix, 0 to 30% EtOAc in hexanes, 15 min) to give 5-(3-chlorophenoxy)-3-iodo-1H-indazole (194 mg, 524 μmol, 84%) as an off-white solid. MS (M+H)+=370.8; 1H NMR (CDCl3) δ: 7.73 (d, J=8.7 Hz, 1H), 7.28 (d, J=5.3 Hz, 1H), 7.22-7.25 (m, 1H), 7.17 (d, J=1.9 Hz, 1H), 7.08 (dt, J=7.9, 0.9 Hz, 1H), 6.98 (t, J=2.3 Hz, 1H), 6.89 (dd, J=8.3, 2.3 Hz, 1H).
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