Sodium Bicarbonate → 2,2,2-Trifluoro-1-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

Participants

Reaction Steps

A mixture of 200 mg (0.45 mmol) of 1-(4-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,2,2-trifluoro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol and 185 mg (2.83 mmol) of zinc powder in acetic acid was warmed at reflux for 30 minutes. The mixture was then cooled and made basic with saturated aqueous sodium bicarbonate and extracted with three 30 mL portions of ethyl acetate. The combined organic layers were washed with two 15 mL portions of saturated aqueous sodium bicarbonate, three 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 145 mg (78%) of the title compound. The material from the column was triturated with ether-hexanes to afford 85 mg of the title compound as a white solid. The solid was dried under house vacuum at 90° C. and then 110° C. MS m/z 410.30 (MH+), m.p. 137° C.-141° C.

Provenance & Evidence