5-bromo-1-(4-fluorophenyl)-1H-benzotriazole → 1-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-benzotriazol-5-yl]ethanol

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 (0.22 mL of a 2.5 M solution in hexanes, 0.55 mmol). After 1 minute, a chilled (−78° C.) solution of 1-[1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indol-3-yl]-2,2,2-trifluoroethanone (185 mg, 0.57 mmol) in 1 mL of THF was added. After 30 minutes, the mixture was quenched with brine solution (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and solvent evaporated in vacuo to afford a yellow oil. The residue was purified by column chromatography over silica gel eluting with 0-60% ethyl acetate in hexanes and fractions corresponding to MS m/z 541 (MH+) peak were pooled and concentrated in vacuo to afford 150 mg of the title compound as a brownish solid.

1. additionwas added
2. waitAfter 30 minutes
3. customthe mixture was quenched with brine solution (50 mL)
4. extractionextracted with ethyl acetate
5. washThe combined organic layers were washed with water
6. dry with materialdried over anhydrous sodium sulfate, and solvent
7. customevaporated in vacuo
8. customto afford a yellow oil
9. customThe residue was purified by column chromatography over silica gel eluting with 0-60% ethyl acetate in hexanes and fractions corresponding to MS m/z 541 (MH+) peak
10. concentrationconcentrated in vacuo

ORD 기록

ord-d7a80266c1f64016a2a106d2eb53ce7c

출처 데이터셋

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08658637B2