2,6-Dibromopyridine → HCID 22180772, compound

HRID 1796076Notes

Reaction equation

HRID 1796076 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[Na].[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[N:3]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 22180772HCID 22180772, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A stirred solution of 2,6-dibromopyridine (2.0 g, 8.3 mmol) and 1,2,4-triazole sodium salt (1.0 g, 9.9 mmol) in dimethylsulfoxide (10 ml) was heated at 60° C. for 5 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-[1,2,4]triazol-1-yl)pyridine (0.84 g) as a white solid: δH (400 MHz, CDCl3) 7.49 (1H, d, J 8), 7.74 (1H, dd, J 8 and 8), 7.87 (1H, d, J 8), 8.09 (1H, s), 9.15 (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-e50726fde56844959515246589ac0676
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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