2-Chloro-3-nitropyridine → 7-Chloro-1H-pyrrolo[2,3-c]pyridine

Temperatur

-78 °C

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.

1. custombefore being quenched with 20% NH4Cl (150 ml)
2. extractionThe aqueous phase was extracted with EtOAc (3×150 ml)
3. dry with materialThe combined organic layer was dried over MgSO4
4. filtrationAfter filtration and concentration
5. customthe crude product was purified by silica gel column chromatography

ORD-Eintrag

ord-ad0ffa5f287d47419e66a71ebd0496d1

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745625B2