Cesium carbonate → 2-(1-phenyl-1H-imidazol-2-yl)pyridine

HRID 2068442Notes

Reaction equation

HRID 2068442 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]>[C:13]1([N:11]2[CH:10]=[CH:9][N:8]=[C:7]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 5893132-(1H-imidazol-2-yl)pyridine

Product 1

HCID 220266192-(1-phenyl-1H-imidazol-2-yl)pyridine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(2-pyridyl)imidazole (6.91 g), iodobenzene (11.47 g), Cs2CO3 (25 g), and copper powder (15 g) were mixed in 60 mL anhydrous DMF in a 250 mL round bottom flask equipped with a magnetic stirrer and a reflux condenser. The mixture is 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 layer was washed with H2O (2×100 mL) and then with saturated NaCl (2×150 mL), and subsequently dried with anhydrous Na2SO4. Evaporation of the solvent gave crude 1-phenyl-2(2-pyridyl)imidazole. 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.

Workup

  1. customequipped with a magnetic stirrer and a reflux condenser
  2. customThe mixture is degassed with N2 for 15 minutes at room temperature
  3. temperaturerefluxed under N2 in an oil bath for 24 hours
  4. filtrationsuction-filtered
  5. customto remove the solid byproduct
  6. extractionThe filtrate was extracted with EtOAc (3×100 mL)
  7. washThe combined organic layer was washed with H2O (2×100 mL)
  8. dry with materialwith saturated NaCl (2×150 mL), and subsequently dried with anhydrous Na2SO4
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-36b990c16c2d4936b7fca75b62de46a9
Source dataset
uspto-grants-2012_10
Patent number
US08298388B2

Reaction notes

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