Reacción #1106670

Ecuación de reacción

1,5-dichloroanthraquinone

Potassium t-butoxide

triisobutylphosphatrane

3-aminopyridine

→

Compound 27

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

Disolventes

Toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe system was flushed with argon
2. 2
   Temperaturaheated
3. 3
   Temperaturato reflux overnight
4. 4
   TemperaturaThe mixture was cooled
5. 5
   Otrothe solvent was removed under vacuum
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   LavadoThe organic layer was washed with water twice
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   OtroAfter the solvent was removed
10. 10
    Otrothe residue was purified by flash chromatography

Procedimiento

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:

Fuente