Реакция #1106670

Уравнение реакции

1,5-dichloroanthraquinone

Potassium t-butoxide

triisobutylphosphatrane

3-aminopyridine

→

Compound 27

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

Растворители

Toluene

Условия реакции

Обработка

1. 1
   ДругоеThe system was flushed with argon
2. 2
   Температураheated
3. 3
   Температураto reflux overnight
4. 4
   ТемператураThe mixture was cooled
5. 5
   Другоеthe solvent was removed under vacuum
6. 6
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
7. 7
   ПромывкаThe organic layer was washed with water twice
8. 8
   Сушкаdried over anhydrous magnesium sulfate
9. 9
   ДругоеAfter the solvent was removed
10. 10
    Другоеthe residue was purified by flash chromatography

Методика

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:

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