反应详情

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.

1. additionwas added
2. temperatureThereafter, reflux
3. customAfter completion of the reaction
4. temperaturethe reaction product was cooled
5. extractionextracted by addition of cold water and toluene
6. washThe organic layer was washed with saline water
7. customdried on magnesium sulfate
8. customfollowed by removal of the solvent under a reduced pressure
9. customto provide
10. customdry solid
11. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)