Réaction #3427

Équation de réaction

3,5-dibromopyridine

phenylboronic acid

sodium carbonate

→

title compound

3-bromo-5-phenylpyridine

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureat reflux for 6 hours
3. 3
   Autrethe solvent was removed
4. 4
   AutreThe residue was purified by chromatography (silica gel
5. 5
   Lavageeluting with ether:hexane 1:10

Mode opératoire

Portions of 3,5-dibromopyridine (1.0 g, 4.22 mmol), phenylboronic acid (570 mg, 4.6 mmol) and palladium tetra(triphenylphosphine) (60 mg) were combined in toluene (20 mL) with aqueous sodium carbonate solution (2M, 3.0 mL) and heated at reflux for 6 hours. The mixture was cooled to ambient temperature, and the solvent was removed. The residue was purified by chromatography (silica gel, eluting with ether:hexane 1:10 to give the title compound: MS (CI/NH3) m/z: 234/236 (M+H)+, 251/153 (M+NH4)+ ; 1H NMR (CDCl3, 300 MHz) δ7.21-8.02 (dd, J=2.0, 2.0 Hz), 8.65 (d, J=2.0 Hz), 8.75 (d, J=2.0 Hz).

Source