Reaction #577216

Reaction equation

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

Yield 43.0%

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThereafter, reflux
3. 3
   OtherAfter completion of the reaction
4. 4
   Temperaturethe reaction product was cooled
5. 5
   Extractionextracted by addition of cold water and toluene
6. 6
   WashThe organic layer was washed with saline water
7. 7
   Otherdried on magnesium sulfate
8. 8
   Otherfollowed by removal of the solvent under a reduced pressure
9. 9
   Otherto provide
10. 10
    Otherdry solid
11. 11
    OtherThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

Procedure

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.

Source