反应 #470383

反应方程式

3,5-dibromo-pyridin

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline

K2CO3

THF

→

white solid

收率 98.4%

3-(5-bromo-pyridin-3-yl)-quinoline

收率 98.4%

溶剂

water

toluene

反应条件

后处理

1. 1
   workup.ADDITIONwere added
2. 2
   萃取the mixture was subject to extraction
3. 3
   萃取Then, an organic layer extracted
4. 4
   其他therefrom was dried
5. 5
   过滤filtered
6. 6
   其他A solvent was removed
7. 7
   其他the resultant was separated

实验过程

1.11 g (4.7 mmol) of 3,5-dibromo-pyridin, 1.0 g (3.92 mmol) of 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline, 0.45 g of tetrakis(triphenylphosphine)palladium(0), 7.84 ml of 2 M K2CO3 and 1.26 g of tetrabutylammoniumbromide were added to a 100 ml round-bottom flask in an argon atmosphere, and 30 ml of THF and 15 ml of toluene were added thereto. Then, the mixture was refluxed at 100° C. for 16 hours. When the mixture solution turned dark brown, water was added thereto and the mixture was subject to extraction using chloroform. Then, an organic layer extracted therefrom was dried using anhydrous magnesium sulfate and filtered. A solvent was removed and the resultant was separated using a silica gel column chromatography to obtain 1.1 g of white solid 3-(5-bromo-pyridin-3-yl)-quinoline which was identified by an atmospheric pressure chemical ionization (APCI) using LCMS (SHIMADZU, LCMS-IT-TOF). As a result, a main peak was observed at [M+H]+=285.

来源