Reacción #7432

Ecuación de reacción

2-Chloro-isoquinoline

phenylboronic acid

triphenylphosphine

potassium carbonate

→

1-phenylisoquinoline

Rendimiento 96.9%

Disolventes

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 17 hrs
2. 2
   TemperaturaThe mixture was then cooled
3. 3
   Otrothe aqueous layer was separated from the organic layer
4. 4
   ExtracciónThe aqueous extraction
5. 5
   Extracciónwas then extracted with ethyl acetate
6. 6
   ExtracciónThe combined organic extractions
7. 7
   Extracciónwere then extracted with brine
8. 8
   Secadodried over magnesium sulfate
9. 9
   OtroThe solvent was then evaporated
10. 10
    Otroto give a liquid which
11. 11
    workup.DISTILLATIONwas then purified by Kugelhor distillation at 220° C. @1200 microns

Procedimiento

2-Chloro-isoquinoline (28.8 g, 0.176 mol), phenylboronic acid (25.7 g 0.211 mol), triphenylphosphine (4.6 g 17.6 mmol), palladium acetate (0.99 g 4.4 mmol) and 2M solution of potassium carbonate (65.7 g 0.475 mol) were added to 270 ml of dimethoxyethane. This mixture was stirred at reflux for 17 hrs. The mixture was then cooled and the aqueous layer was separated from the organic layer. The aqueous extraction was then extracted with ethyl acetate. The combined organic extractions were then extracted with brine and dried over magnesium sulfate. The solvent was then evaporated to give a liquid which was then purified by Kugelhor distillation at 220° C. @1200 microns to yield 35 g (96.9%) of 1-phenylisoquinoline.

Fuente