Reaction #2044990

Reaction equation

2-(1H-imidazol-2-yl)pyridine

iodobenzene

Cs2CO3

→

2-(1-phenyl-1H-imidazol-2-yl)pyridine

Solvents

DMF

Conditions

Workup

1. 1
   Otherequipped with a magnetic stirrer and a reflux condenser
2. 2
   OtherThe mixture was degassed with N2 for 15 minutes at room temperature
3. 3
   Temperaturerefluxed under N2 in an oil bath for 24 hours
4. 4
   Filtrationsuction-filtered
5. 5
   Otherto remove the solid byproduct
6. 6
   ExtractionThe filtrate was extracted with EtOAc (3×100 mL)
7. 7
   WashThe combined organic layers were washed with H2O (2×100 mL)
8. 8
   Dryingwith saturated NaCl (2×150 mL), and subsequently dried with anhydrous Na2SO4
9. 9
   OtherEvaporation of the solvent

Procedure

2-(1H-imidazol-2-yl)pyridine (6.91 g), iodobenzene (11.47 g), Cs2CO3 (25 g), and copper powder (15 g) were combined in 60 mL anhydrous DMF in a 250 mL round bottom flask equipped with a magnetic stirrer and a reflux condenser. The mixture was degassed with N2 for 15 minutes at room temperature and then refluxed under N2 in an oil bath for 24 hours. The resulting mixture was cooled to room temperature and suction-filtered to remove the solid byproduct. The filtrate was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (2×100 mL), then with saturated NaCl (2×150 mL), and subsequently dried with anhydrous Na2SO4. Evaporation of the solvent gave crude 2-(1-phenyl-1H-imidazol-2-yl)pyridine. The crude product is generally pure enough to use in making redox mediators, although the crude product may be further purified using a silica gel column and eluting with MeOH/CHCl3.

Source