Reaction #577217

Reaction equation

sodium carbonate

9,9-dimethylfluorene-2-boronic acid

1-chloroisoquinoline

toluene

→

1-(9,9-dimethylfluorene-2-yl)isoquinoline

Yield 54.3%

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: toluene/ethyl acetate=50/1)

Procedure

In a 100 ml-three-necked flask, 2.91 g (12.2 mmole) of 9,9-dimethylfluorene-2-boronic acid, 2.00 g (12.2 mmole) of 1-chloroisoquinoline, 10 ml of toluene, 5 ml of ethanol and 10 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.44 g (0.38 mmole) of tetrakis(triphenylphosphine)palladium (0) was added thereto. Thereafter, reflux under stirring was performed for 5 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: toluene/ethyl acetate=50/1) to obtain 2.13 g (yield=54.2%) of 1-(9,9-dimethylfluorene-2-yl)isoquinoline.

Source