Reaction #1106670

Reaction equation

1,5-dichloroanthraquinone

Potassium t-butoxide

triisobutylphosphatrane

3-aminopyridine

→

Compound 27

1,5-bis(pyridin-3-ylamino)anthracene-9,10-dione

Solvents

Toluene

Conditions

Workup

1. 1
   OtherThe system was flushed with argon
2. 2
   Temperatureheated
3. 3
   Temperatureto reflux overnight
4. 4
   TemperatureThe mixture was cooled
5. 5
   Otherthe solvent was removed under vacuum
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   WashThe organic layer was washed with water twice
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   OtherAfter the solvent was removed
10. 10
    Otherthe residue was purified by flash chromatography

Procedure

Potassium t-butoxide (3.37 g, 30 mmol) and Pd2(dba)3 (0.55 g, 0.6 mmol) were added to a 100 mL round bottom flask. Toluene (50 mL) and triisobutylphosphatrane (0.82 g, 2.4 mmol) were then added, followed by 3-aminopyridine (1.88 g, 20 mmol) and 1,5-dichloroanthraquinone (2.77 g, 10 mmol). The system was flushed with argon and heated to reflux overnight. The mixture was cooled and the solvent was removed under vacuum. The residue was dissolved in dichloromethane and water. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. After the solvent was removed, the residue was purified by flash chromatography to provide Compound 27 as a red solid. The structure of Compound 27 is given below:

Source