2,6-Dibromopyridine → 2-Bromo-6-(1H-imidazol-1-yl)pyridine

HRID 1796065Notes

Reaction equation

HRID 1796065 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Na].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>CS(C)=O.O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[N:3]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 57373095Imidazole sodium

Product 1

HCID 221807822-Bromo-6-(1H-imidazol-1-yl)pyridineYield 9.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2,6-dibromopyridine (2.0 g, 8.3 mmol) and imidazole sodium salt (1.0 g, 10.5 mmol) in dimethylsulfoxide (10 ml) was heated at 100° C. for 36 h. After cooling to ambient temperature the reaction was diluted with water and extracted into dichloromethane. Combined organic extracts were washed with water and saturated brine then dried over magnesium sulfate, filtered and evaporated in vacuo to give a solid. Purification by chromatography on silica gel eluting with dichloromethane, then dichloromethane containing 5% methanol, gave 2-bromo-6-(1H-imidazol-1-yl)pyridine (0.18 g) as an off-white solid: δH (400 MHz, CDCl3) 7.20 (1H, m), 7.32 (1H, d, J 8), 7.47 (1H, d, J 8), 7.62 (1H, m), 7.68 (1H, dd, J 8 and 8), 8.35 (1H, s); m/z (ES+) 224/226 (M++H).

Workup

  1. extractionextracted into dichloromethane
  2. washCombined organic extracts were washed with water and saturated brine
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a solid
  7. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-3d7edf99db0243deb84743dcff43c770
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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