Ethyl Acetate → HCID 59526026, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of methyl[4-(6-bromopyridin-2-yl)-1H-pyrazol-1-yl]acetate (196 mg, 0.66 mmol) in tetrahydrofuran (3.4 mL) was added diisobutylaluminum hydride (1.0M in hexane, 1.99 mL, 1.99 mmol) dropwise. The solution was allowed to warm to room temperature and maintained at room temperature overnight. Additional diisobutylaluminum hydride (0.66 mL, 0.66 mmol) was then added and the reaction was stirred for another 24 hours. Saturated aqueous potassium sodium tartrate (20 mL) was then added and the solution was vigorously stirred for three hours. Ethyl acetate (7 mL) was added to the solution, and it was stirred another 60 minutes. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (0-5% methanol in ethyl acetate) afforded the title compound.

Provenance & Evidence