反応 #57281

反応方程式

chlorotrimethylsilane

n-BuLi

N,N-diisopropylamine

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

→

title product

収率 82.0%

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

収率 82.0%

溶媒

THF

THF

反応条件

後処理

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
   その他the reaction was quenched with saturated NH4Cl(aq) (10 ml)
4. 4
   その他partitioned between water and EtOAc
5. 5
   抽出The aqueous phase was further extracted with EtOAc
6. 6
   洗浄washed with brine
7. 7
   乾燥dried (MgSO4)
8. 8
   濃縮concentrated
9. 9
   その他purified by silica gel chromatography (isocratic CHCl3)

実験手順

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.

出典