Reacción #577218

Ecuación de reacción

sodium carbonate

4-methylphenyl-boronic acid

1-chloroisoquinoline

toluene

→

1-(4-methylphenyl)isoquinoline

Rendimiento 51.1%

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 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 The residue
11. 11
    Otrowas purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Procedimiento

In a 200 ml-three-necked flask, 3.40 g (25.0 mmole) of 4-methylphenyl-boronic acid (made by Aldrich Co.), 4.09 g (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 mol 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 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 2.80 g (yield=51.1%) of 1-(4-methylphenyl)isoquinoline.

Fuente