Acetone → HCID 58852277, compound

Participants

Reaction Steps

To a solution of 6-fluoro-1-[1-(5-fluoro-indan-2-ylmethyl)-piperidin-4-yl]-5-methyl-1H-benzoimidazole (25 mg, 0.065 mmol) in anhydrous THF (2 mL) was added tert-BuLi (0.058 mL, 1.7 M in pentane) at −78° C. After stirring for 10 minutes, anhydrous acetone (0.008 mL) was added and the reaction mixture was stirred at −78° C. for 40 minutes. After quenching with 1 M HCl (0.2 mL) the mixture was allowed to warm to rt. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate. The organic layers were washed with saturated NaHCO3, brine, and dried over Na2SO4. The extracts were removed and the residue was purified by flash chromatography (20/1 CH2Cl2/CH3OH) to afford 2-{6-fluoro-1-[1-(5-fluoro-indan-2-ylmethyl)-piperidin-4-yl]-5-methyl-1H-benzoimidazol-2-yl}-propan-2-ol (5 mg, 17%) as a white solid.

Provenance & Evidence