Reacción #57277

Ecuación de reacción

1,1-dimethylethyl-4-oxo-1-piperidinecarboxylate

n-BuLi

isopropylamine

4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

→

title compound

Rendimiento 85.0%

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

Rendimiento 85.0%

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.WAITAfter an additional 1.5 h at −78° C.
3. 3
   Temperaturathe reaction mixture was warmed to room temperature
4. 4
   Otroquenched with saturated NH4Cl(aq)
5. 5
   ExtracciónExtraction with EtOAc (3□)
6. 6
   Lavadowashing with brine
7. 7
   Otrodrying
8. 8
   Filtración(Na2SO4), filtration
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    Otroprovided crude material which
11. 11
    Otrowas purified by flash chromatography (120 g SiO2, 0-5% EtOAc in CHCl3)

Procedimiento

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 (120 g SiO2, 0-5% EtOAc in CHCl3) to give the title compound as a white solid (85%). ESMS [M+H]+: 536.0.

Fuente