Iodoacetamide → 2-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[2,3-b]pyridin-1-yl)acetamide

Participants

Reaction Steps

To a solution of 60 mg (0.14 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol in 2 mL of DMF was added 21 mg (0.27 mmol) of powdered KOH followed by 51 mg (0.28 mmol) of iodoacetamide. The mixture stirred for 30 minutes, and was then diluted with saturated aqueous ammonium chloride and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with two 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel using dichloromethane to load the sample and then eluting with dichloromethane and then ethyl acetate. The material from the column was triturated with ether-hexanes and dried under house vacuum at 80° C. for 2 hours to afford 21 mg (30%) of the title compound. MS m/z 484.28 (MH+).

Provenance & Evidence