Ethyl bromoacetate → (3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[2,3-b]pyridin-1-yl)acetic acid

Participants

Reaction Steps

To a solution of 110.0 mg (0.26 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 16 mg (0.4 mmol) of 60% sodium hydride in mineral oil followed by 32 μL (0.29 mmol) of ethyl bromoacetate. The reaction was monitored by TLC (ethyl acetate) indicating a new polar product. The reaction was diluted with methanol and made basic with 2N aqueous sodium hydroxide. The mixture stirred for 1 hour and was then monitored by LCMS indicating a mass corresponding to the carboxylic acid (M+=485.30). The reaction was diluted with 7 mL of saturated aqueous ammonium chloride and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 110 mg (88%) of (3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[2,3-b]pyridin-1-yl)acetic acid which was used without further purification.

Provenance & Evidence