Реакция #577216

Уравнение реакции

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

Выход 43.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   ТемператураThereafter, reflux
3. 3
   ДругоеAfter completion of the reaction
4. 4
   Температураthe reaction product was cooled
5. 5
   Экстракцияextracted by addition of cold water and toluene
6. 6
   ПромывкаThe organic layer was washed with saline water
7. 7
   Другоеdried on magnesium sulfate
8. 8
   Другоеfollowed by removal of the solvent under a reduced pressure
9. 9
   Другоеto provide
10. 10
    Другоеdry solid
11. 11
    ДругоеThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

Методика

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.

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