반응 #470385

반응 방정식

3,5-dibromo-pyridin

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

K2CO3

THF

→

white solid

수율 98.4%

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

수율 98.4%

용매

water

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   추출the mixture was subject to extraction
3. 3
   추출Then, an organic layer extracted
4. 4
   기타therefrom was dried
5. 5
   여과filtered
6. 6
   기타A solvent was removed
7. 7
   기타the resultant was separated

실험 절차

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.

출처