Reacción #1559693

Ecuación de reacción

8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid

sodium carbonate

3-bromo-9-phenyl-9H-carbazole

tri-o-tolylphosphine

→

8,8-Dimethyl-3-(9-phenyl-9H-carbazol-3-yl)-8H-10,12b-diaza-benzo[a]aceanthrylene

Disolventes

toluene

water

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture is heated
2. 2
   Temperaturaunder reflux for 16 h
3. 3
   TemperaturaAfter cooling
4. 4
   Otrothe organic phase is separated off
5. 5
   Filtraciónfiltered through silica gel
6. 6
   Lavadowashed three times with 200 ml of water each time
7. 7
   Otrosubsequently evaporated to dryness
8. 8
   OtroThe residue is recrystallised from toluene and from CH2Cl2/isopropanol

Procedimiento

36 g (110 mmol) of 8,8-dimethyl-8H-10,12b-diazabenzo[a]aceanthrylene-3-boronic acid, 35 g (110 mmol) of 3-bromo-9-phenyl-9H-carbazole and 9.7 g (92 mmol) of sodium carbonate are suspended in 350 ml of toluene, 350 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water each time and subsequently evaporated to dryness. The residue is recrystallised from toluene and from CH2Cl2/isopropanol and finally sublimed in a high vacuum. Yield: 50 g (99 mmol), 89% of theory, purity according to HPLC 99.9%.

Fuente