反应 #659306

反应方程式

2,8-dichloroquinoline-3-carbaldehyde

Na2CO3

phenylboronic acid

→

title compound

收率 97.1%

8-Chloro-2-phenylquinoline-3-carbaldehyde

收率 97.1%

溶剂

DME

反应条件

后处理

1. 1
   其他was degassed
2. 2
   温度to cool to room temperature
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   洗涤washed with brine
5. 5
   干燥The organic layer was dried (MgSO4)
6. 6
   其他the solvent was removed under reduced pressure
7. 7
   其他The resultant solid was triturated in ether
8. 8
   过滤filtered
9. 9
   洗涤washed with small amount of ether
10. 10
    干燥light petroleum, and dried

实验过程

A mixture of 2,8-dichloroquinoline-3-carbaldehyde (2.0 g, 8.85 mmol), 2M aqueous Na2CO3 solution (8 mL), phenylboronic acid (1.5 g, 12.3 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.25 g, 0.216 mmol) in DME (30 mL) was degassed and the mixture heated at 110° C. for 4 h. The mixture was allowed to cool to room temperature, diluted with EtOAc and washed with brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The resultant solid was triturated in ether, filtered, washed with small amount of ether, then light petroleum, and dried, to give the title compound (2.3 g, 97%) as an off-white solid. δH (CDCl3) 10.25 (s, 1H), 8.86 (s, 1H), 7.95-8.02 (m, 2H), 7.78-7.14 (m, 2H), 7.54-7.62 (m, 4H). LCMS (ES+) 268 (M+H)+, RT 1.98 minutes.

来源