Reaction #470385

Reaction equation

3,5-dibromo-pyridin

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

K2CO3

THF

→

white solid

Yield 98.4%

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

Yield 98.4%

Solvents

water

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Extractionthe mixture was subject to extraction
3. 3
   ExtractionThen, an organic layer extracted
4. 4
   Othertherefrom was dried
5. 5
   Filtrationfiltered
6. 6
   OtherA solvent was removed
7. 7
   Otherthe resultant was separated

Procedure

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.

Source