反応 #2006468

反応方程式

2-Chloro-3-nitropyridine

vinyl magnesium bromide

→

7-chloro-6-azaindole

収率 31.0%

溶媒

THF

反応条件

後処理

1. 1
   その他before being quenched with 20% NH4Cl (150 ml)
2. 2
   抽出The aqueous phase was extracted with EtOAc (3×150 ml)
3. 3
   乾燥The combined organic layer was dried over MgSO4
4. 4
   ろ過After filtration and concentration
5. 5
   その他the crude product was purified by silica gel column chromatography

実験手順

2-Chloro-3-nitropyridine 22e (5.0 g) was dissolved in dry THF (200 ml). After the solution was cooled down to −78° C., an excess of vinyl magnesium bromide (1.0 M in THF, 100 ml) was added. Then, the reaction was left at −20° C. for eight hours before being quenched with 20% NH4Cl (150 ml). The aqueous phase was extracted with EtOAc (3×150 ml). The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford 1.5 g of 7-chloro-6-azaindole 1e in 31% yield.

出典