Acetic Acid → HCID 24962016, compound

Participants

Reaction Steps

To a chilled (0° C.) solution of 100 mg (0.21 mmol) of 3-(3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propionaldehyde (prepared according to methods described in Examples 34 and 35) in dichloroethane was added 160 mg (2.6 mmol) acetic acid and 300 mg (2.6 mmol) 4-piperidinemethanol. The solution was warmed to room temperature, stirred for 30 minutes, and 0.1 g (0.5 mmol) of sodium triacetoxyborohydride was added. The solution was stirred at room temperature overnight. The reaction was diluted with water and extracted with ethyl acetate, the aqueous layer was separated and the organic layers were combined and washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-HPLC to afford 42 mg (34.8%) of the title compound. MS m/z 581.6 (MH+).

Provenance & Evidence