Реакция #470385

Уравнение реакции

3,5-dibromo-pyridin

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

K2CO3

THF

→

white solid

Выход 98.4%

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

Выход 98.4%

Растворители

water

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   Экстракцияthe mixture was subject to extraction
3. 3
   ЭкстракцияThen, an organic layer extracted
4. 4
   Другоеtherefrom was dried
5. 5
   Фильтрацияfiltered
6. 6
   ДругоеA solvent was removed
7. 7
   Другоеthe resultant was separated

Методика

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.

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