To a chilled (−78° C.) solution of 241 mg (1.13 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone in 5 mL of anhydrous THF was added 45 mg (1.13 mmol) of 60% NaH in mineral oil. In another flask, 452 μL (1.13 mmol) of n-BuLi was then added to a chilled (−78° C.) solution of 310 mg (1.13 mmol) of 5-bromo-1-pyridin-3-yl-1H-indazole in 10 mL of THF. After 1 minute, the sodium salt of 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone was added to the indazole anion via a cannula. After 1 hour, the mixture was diluted with 25 mL of saturated aqueous ammonium chloride and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with three 10 mL portions of brine, dried over magnesium sulfate, filtered and concentrated. The crude material was purified using Combiflash chromatography using EtOAc-hexanes (0-70% gradient) to afford 45 mg (10%) of 2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(1-pyridin-3-yl-1H-indazol-5-yl)ethanol as a colorless solid.
