Iodoacetamide → 2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide

Participants

Reaction Steps

To a chilled (0° C.) solution of 45 mg (0.11 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol in 5 mL of DMF was added 13 mg (0.17 mmol) of powder KOH followed by 31 mg (0.17 mmol) of iodoacetamide. The mixture was stirred over night at room temperature, poured onto ice water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were dried over sodium sulfate, adsorbed on to silica gel and purified by Combiflash chromatography using EtOAc/hexanes (0-80% gradient, product eluted at 40% EtOAc) to provide a colorless film. The material from the column was crystallized from EtOAc-hexanes to afford 20 mg (39%) of the title compound as a colorless powder.

Provenance & Evidence