Reacción #57281

Ecuación de reacción

chlorotrimethylsilane

n-BuLi

N,N-diisopropylamine

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

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title product

Rendimiento 82.0%

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

Rendimiento 82.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter an additional 2 hours of stirring at −78° C.
2. 2
   workup.STIRRINGAfter 1 hour of stirring at −78° C.
3. 3
   Otrothe reaction was quenched with saturated NH4Cl(aq) (10 ml)
4. 4
   Otropartitioned between water and EtOAc
5. 5
   ExtracciónThe aqueous phase was further extracted with EtOAc
6. 6
   Lavadowashed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Concentraciónconcentrated
9. 9
   Otropurified by silica gel chromatography (isocratic CHCl3)

Procedimiento

A solution of N,N-diisopropylamine (3.6 mmol) in THF (9 ml) was cooled to −78° C. under a nitrogen atmosphere. A solution of n-BuLi (2.5M in hexanes, 3.3 mmol) was added dropwise over 3 minutes. After 30 minutes of stirring, a solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.1 mmol) in THF (9 ml) was added dropwise over 9 minutes. After an additional 2 hours of stirring at −78° C., chlorotrimethylsilane (3.1 mmol) was added dropwise over 1 minute. After 1 hour of stirring at −78° C., the reaction was quenched with saturated NH4Cl(aq) (10 ml), warmed to room temperature, and partitioned between water and EtOAc. The aqueous phase was further extracted with EtOAc and the organic layers combined, washed with brine, dried (MgSO4), concentrated, and purified by silica gel chromatography (isocratic CHCl3) to give the title product as a white solid (82%). ESMS [M+H]+: 410.8.

Fuente