5-bromo-1-(4-fluorophenyl)-1H-indazole → 3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[2,3-b]pyridine-1-sulfonic acid dimethylamide

Participants

Reaction Steps

To a chilled (−78° C.) solution of 80 mg (0.27 mmol) of 5-bromo-1-(4-fluorophenyl)-1H-indazole in 1 mL of anhydrous THF was added 110 μL (0.28 mmol) of a solution of 2.5 M n-BuLi in hexane in one portion. This solution was then added to a chilled (−78° C.) solution of 88 mg (0.27 mmol) of 3-(2,2,2-trifluoro-acetyl)pyrrolo[2,3-b]pyridine-1-sulfonic acid dimethylamide in 3 mL of THF. The reaction was monitored by TLC (ethyl acetate-hexanes 4:6). After 30 minutes, the mixture was diluted with 7 mL of saturated aqueous ammonium chloride and extracted with three 10 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 in vacuo. The crude residue was chromatographed on silica gel (prep. plate, 2×1 mm, ethyl acetate-hexanes 30:70). The material from the prep plate was washed from the silica gel with ethyl acetate and concentrated. The residue was triturated with ether-hexanes to afford 42 mg (28%) of the title compound. MS m/z 534.22 (MH+).

Provenance & Evidence