C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[N:9]=[C:8]2[I:15])=O.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[I:15][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([CH2:3][OH:2])[CH:6]=2)[N:10]([CH3:14])[N:9]=1To a solution of 3-iodo-1-methyl-1H-indazole-5-carboxylic acid methyl ester (0.95 g, 3.01 mmol) in CH2Cl2 (30 mL) at 0° C. was slowly added DIBAL-H (1.18 mL, 6.61 mmol). The reaction mixture was stirred at 0° C. for 1.5 h. Carefully quenched with MeOH (1 mL) then diluted with CH2Cl2 (20 mL) and added saturated aqueous Na+K+ tartrate (30 mL). The biphasic mixture was stirred vigorously at room temp for 1 h. The layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organics were washed with water then dried over MgSO4 and concentrated to afford 810 mg of (3-iodo-1-methyl-1H-indazol-5-yl)methanol as a yellow waxy solid.
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