Réaction #2006468

Équation de réaction

2-Chloro-3-nitropyridine

vinyl magnesium bromide

→

7-chloro-6-azaindole

Rendement 31.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrebefore being quenched with 20% NH4Cl (150 ml)
2. 2
   ExtractionThe aqueous phase was extracted with EtOAc (3×150 ml)
3. 3
   SéchageThe combined organic layer was dried over MgSO4
4. 4
   FiltrationAfter filtration and concentration
5. 5
   Autrethe crude product was purified by silica gel column chromatography

Mode opératoire

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.

Source