1-Methyl-3-(trifluoroacetyl)-1H-indole → 2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]-1-(1-methyl-1H-indol-3-yl)ethanol

Participants

Reaction Steps

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-1H-benzotriazole (145 mg, 0.5 mmol) in anhydrous THF (3 mL) was added n-butyllithium (0.25 mL of a 2.5 M solution in hexanes, 0.625 mmol) over a 1 minute period followed by a chilled (−78° C.) solution of 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone (170 mg, 0.75 mmol) in 1 mL of THF. After 15 minutes, the mixture quenched with brine (50 mL) and extracted with three 50 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford a yellow oil. The residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in hexanes to afford 40 mg of the title compound as a light yellow solid. MS m/z 441 (MH+).

Provenance & Evidence