Reacción #1869189

ord-3322c82fa1d54539995fdfa8f5ce8b6b

Ecuación de reacción

N#Cc1ccc2nccc(Br)c2c1
( c )
N#Cc1ccc2nccc(Br)c2c1
4-Bromo-quinoline-6-carbonitrile
C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
vinyltributyltin
C=Cc1ccnc2ccc(C#N)cc12
product
Rendimiento 64.5%
C=Cc1ccnc2ccc(C#N)cc12
4-Vinyl-quinoline-6-carbonitrile
Rendimiento 64.5%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe mixture was refluxed under argon for 2 hours
  2. 2
    OtroEvaporation and flash silica chromatography
  3. 3
    Lavadoeluting with chloroform

Procedimiento

To a solution of (c) (1 g, 4.3 mmol) and vinyltributyltin (1.5 mL, 5.17 mmol) in degassed toluene (20 ml) was added tetrakis(triphenylphosphine) palladium (0) (245 mg, 5 mol %) and the mixture was refluxed under argon for 2 hours. Evaporation and flash silica chromatography eluting with chloroform afforded the product as a pale yellow solid (500 mg, 64%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07498326B2uspto-grants-2009_03