Reacción #331825

Ecuación de reacción

hydrochloric acid

n-butyl lithium

N-boc-2-aminopicoline

N-methyl-N-(methyloxy)cyclopropanecarboxamide

→

title compound

Rendimiento 100.8%

2-Cyclopropyl-1H-pyrrolo[2,3-b]pyridine

Rendimiento 100.8%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added, under an atmosphere of nitrogen
2. 2
   Otrothe temperature below 0° C
3. 3
   Temperaturathen warmed to 10° C.
4. 4
   TemperaturaThe mixture was heated at 60° C. for 2 h
5. 5
   Temperaturacooled
6. 6
   Otrothe aqueous layer separated
7. 7
   workup.ADDITIONThe aqueous layer was basified by the addition of 10M sodium hydroxide, with ice/water cooling, until the pH was 10-12
8. 8
   ExtracciónThe resulting mixture was extracted with DCM (2×100 ml)
9. 9
   Lavadothe combined organic extracts were washed with water (50 ml)
10. 10
    Otrodried
11. 11
    Otroevaporated

Procedimiento

To a stirred mixture of N-boc-2-aminopicoline (10.4 g) in dry THF (70 ml) in an ice/salt bath was added, under an atmosphere of nitrogen, n-butyl lithium (2M solution in cyclohexane, 50 ml), keeping the temperature below 0° C. The reaction was stirred below 0° C. for 1 h before the addition of a solution of N-methyl-N-(methyloxy)cyclopropanecarboxamide (7.5 g) (available from Pfaltz-Bauer) in dry THF (20 ml). The reaction mixture was stirred at 0° C. for 2 h then warmed to 10° C. and poured into 5M hydrochloric acid (130 ml). The mixture was heated at 60° C. for 2 h, cooled and the aqueous layer separated. The aqueous layer was basified by the addition of 10M sodium hydroxide, with ice/water cooling, until the pH was 10-12. The resulting mixture was extracted with DCM (2×100 ml) and the combined organic extracts were washed with water (50 ml), dried using a hydrophobic frit and evaporated to give the title compound (7.89 g).

Fuente