CO[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4].CC(C[AlH]C[CH:21]([CH3:23])[CH3:22])C.[CH3:24][CH2:25][O:26]C(C)=O>C(Cl)Cl>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:3][OH:4])=[N:6][N:7]2[CH:22]2[CH2:21][CH2:23][CH2:24][CH2:25][O:26]2)=[CH:12][CH:11]=1To a solution of 6-Chloro-1H-indazole-3-carboxylic acid methyl ester (2.94 g, 10.0 mmol) in dry CH2Cl2 (50 mL) cooled to −78 degrees Celsius was added DIBAL-H (3.56 mL, 20.0 mmol) slowly. After the addition was complete, the reaction was allowed to warm to room temperature, where HPLC showed that there was a remaining 10% starting material. Extra DIBAL-H (0.35 mL) was then added and stirred for 10 minutes. The reaction was diluted with EtOAc (1000 mL) and washed with 1 N HCl (2×100 mL). It was further washed with 1 N NaHCO3 (100 mL), and then with saturated NaCl (100 mL). The organic was dried over Mg SO4, filtered, and then concentrated to a white solid (2.65 g, 99.5%).
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