2-Bromo-3-methylpyridine → 3-Methyl-2,2'-bipyridine

HRID 1926491Notes

Reaction equation

HRID 1926491 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1>O1CCCC1>[CH3:8][C:7]1[C:2]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 2208322-Bromo-3-methylpyridine

Product 1

HCID 1824573-Methyl-2,2'-bipyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask were added 1.0 g 2-bromo-3-methylpyridine and 10 ml of dry tetrahydrofuran. The solution was purged with nitrogen and 34 mg tetrakis(triphenylphosphine)palladium was added followed by 17.4 ml of a 0.5M solution of 2-pyridylzinc bromide in tetrahydrofuran. The mixture was stirred at 22 C for 24 hours, then 40 C for 72 hours. The mixture was poured into a solution of 5 g EDTA, 2 g sodium carbonate and 40 ml water. The product was extracted twice with diethylether, washed with water and dried over sodium sulfate. Following filtration and solvent removal, the product was purified by silica gel chromatography using 48% ethyl acetate, 48% hexane and 4% methanol. A slightly yellow oil remained 0.38 g.

Workup

  1. customThe solution was purged with nitrogen and 34 mg tetrakis(triphenylphosphine)palladium
  2. additionwas added
  3. wait40 C for 72 hours
  4. additionThe mixture was poured into a solution of 5 g EDTA, 2 g sodium carbonate and 40 ml water
  5. extractionThe product was extracted twice with diethylether
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltration and solvent removal
  9. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-73f579e68d93435ca11fbd46f280c362
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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