5-bromo-1-(4-fluorophenyl)-1H-indazole → 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-1H-indazole (2.0 g, 6.8 mmol, 1.2 equiv.) in 20 mL of THF was added n-BuLi (2.5 mL, 6.2 mmol, 1.1 equiv.) followed by a chilled (−78° C.) solution of 1-allyl-4-(2,2,2-trifluoroacetyl)-1H-pyrrole-2-carboxylic acid ethyl ester (1.6 g, 5.7 mmol, 1.0 equiv.) in 3 mL of THF in one portion. After 30 minutes, the mixture was quenched with water, warmed to room temperature, diluted with brine, and extracted with EtOAc. The combined organics were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (5-30% EtOAc-hexanes) to provide 890 mg (32%) of the title compound as a pale orange solid. MS m/z 488.30 (MH+).

Provenance & Evidence