Reaction #2320124

Reaction equation

6-bromo-3-methylpyridine

phenylboronic acid

triphenylphosphine

K2CO3

→

3-methyl-6-phenylpyridine

Yield 84.1%

Solvents

dimethoxyethane

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Temperatureat reflux for 20 hours
3. 3
   ExtractionThe aqueous phase was extracted twice with 200 mL of ethyl acetate
4. 4
   ExtractionThe combined organic extractions
5. 5
   Extractionwere then extracted with brine
6. 6
   Dryingdried over magnesium sulfate
7. 7
   OtherThe filtrate was evaporated in vacuo
8. 8
   workup.DISTILLATIONthe resultant oil purified by Kugelehor distillation (190° C. @ 500 microns)

Procedure

To a 2 L flask, 45.0 g (262 mmol) of 6-bromo-3-methylpyridine, 38.3 g (314 mmol) of phenylboronic acid, 1.47 g (6.54 mmol) of palladium acetate, 6.86 g (26.2 mmol) of triphenylphosphine and 353 mL of 2M K2CO3 were added to 405 mL of dimethoxyethane. The mixture was heated at reflux for 20 hours and cooled to room temperature. The aqueous phase was extracted twice with 200 mL of ethyl acetate. The combined organic extractions were then extracted with brine and dried over magnesium sulfate. The filtrate was evaporated in vacuo and the resultant oil purified by Kugelehor distillation (190° C. @ 500 microns) to give 37.2 g (84.1% yield) of 3-methyl-6-phenylpyridine as white solids.

Source