Ethyl Acetate → [6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazol-3-yl]-methanol

Participants

Reaction Steps

To 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%).

Provenance & Evidence