反応 #721722

反応方程式

9-phenyl-9H,9′H-3,3′-bicarbazole

4-chlorobenzo[4,5]thieno[3,2-d]pyrimidine

dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine

sodium 2-methylpropan-2-olate

→

4-(9′-phenyl-9H,9′H-[3,3′-bicarbazol]-9-yl)benzo[4,5]thieno[3,2-d]pyrimidine

収率 44.0%

溶媒

m-Xylene

反応条件

後処理

1. 1
   その他degassed with nitrogen
2. 2
   温度heated
3. 3
   その他The reaction was quenched with aqueous ammonium chloride
4. 4
   ろ過filtered through a plug of Celite® with dichloromethane (DCM)
5. 5
   その他The crude was purified by column chromatography
6. 6
   その他recrystallized from toluene/ethanol

実験手順

9-phenyl-9H,9′H-3,3′-bicarbazole (3.05 g, 7.47 mmol), 4-chlorobenzo[4,5]thieno[3,2-d]pyrimidine (1.812 g, 8.21 mmol), Pd2dba3 (0.342 g, 0.373 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (S-Phos) (0.307 g, 0.747 mmol), and sodium 2-methylpropan-2-olate (1.794 g, 18.67 mmol) were charged to a 250 mL RBF, diluted in m-Xylene (Volume: 74.7 mL), degassed with nitrogen and heated to reflux at 150° C. overnight. The reaction was quenched with aqueous ammonium chloride and filtered through a plug of Celite® with dichloromethane (DCM). The crude was purified by column chromatography and then recrystallized from toluene/ethanol to give 4-(9′-phenyl-9H,9′H-[3,3′-bicarbazol]-9-yl)benzo[4,5]thieno[3,2-d]pyrimidine (1.95 g, 44% yield).

出典