Reacción #577216

Ecuación de reacción

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

Rendimiento 43.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturaThereafter, reflux
3. 3
   OtroAfter completion of the reaction
4. 4
   Temperaturathe reaction product was cooled
5. 5
   Extracciónextracted by addition of cold water and toluene
6. 6
   LavadoThe organic layer was washed with saline water
7. 7
   Otrodried on magnesium sulfate
8. 8
   Otrofollowed by removal of the solvent under a reduced pressure
9. 9
   Otroto provide
10. 10
    Otrodry solid
11. 11
    OtroThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

Procedimiento

In a 100 ml-three-necked flask, 3.04 g (24.9 mmole) of phenylboronic acid (made by Tokyo Kasei), 4.0 g of (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.98 g (0.85 mmole) of tetrakis(triphenylphosphine)palladium (0) was added thereto. Thereafter, reflux under stirring was performed for 8 hours under nitrogen stream. After completion of the reaction, the reaction product was cooled and extracted by addition of cold water and toluene. The organic layer was washed with saline water and dried on magnesium sulfate, followed by removal of the solvent under a reduced pressure to provide dry solid. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1) to obtain 2.20 g (yield=43.0%) of 1-phenylisoquinoline. FIG. 7 shows a 1H-NMR spectrum of a solution of the compound in heavy chloroform.

Fuente