Isopropylamine → 1,1-dimethylethyl 4-[4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-4-hydroxy-1-piperidinecarboxylate

온도

-78 °C

To a solution of isopropylamine (5.5 mmol) in THF (15 mL) cooled to −78° C. was added n-BuLi (2.5 M in hexanes, 5.5 mmol) dropwise. After stirring at −78° C. for 20 min a solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (5.0 mmol) in THF (5.0 mL) was added dropwise. The resulting orange solution was stirred at −78° C. for 2 h, followed by dropwise addition of a solution of 1,1-dimethylethyl-4-oxo-1-piperidinecarboxylate (6.1 mmol) in THF (5.0 mL). After an additional 1.5 h at −78° C., the reaction mixture was warmed to room temperature and quenched with saturated NH4Cl(aq). Extraction with EtOAc (3□), washing with brine, drying (Na2SO4), filtration and concentrated in vacuo provided crude material which was purified by flash chromatography (120g SiO2, 0-5% EtOAc in CHCl3) to give the title compound as a white solid (85%). ESMS [M+H]+: 536.0.

1. additionwas added dropwise
2. waitAfter an additional 1.5 h at −78° C.
3. temperaturethe reaction mixture was warmed to room temperature
4. customquenched with saturated NH4Cl(aq)
5. extractionExtraction with EtOAc (3□)
6. washwashing with brine
7. customdrying
8. filtration(Na2SO4), filtration
9. concentrationconcentrated in vacuo
10. customprovided crude material which
11. customwas purified by flash chromatography (120g SiO2, 0-5% EtOAc in CHCl3)

ORD 기록

ord-47cd2993aebd4cb4b2e479987004ed2a

출처 데이터셋

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07282588B2