3,5-Dibromo-2-methoxypyridine → 3-(2-Pyridyl)-5-bromo-2-methoxypyridine

HRID 229644Notes

Reaction equation

HRID 229644 reaction equation
Br[C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1>CN(C)C=O>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

3

Reactant 1

HCID 135677523,5-Dibromo-2-methoxypyridine

Product 1

HCID 223189543-(2-Pyridyl)-5-bromo-2-methoxypyridineYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

100 ml of a dimethylformamide solution containing 6.3 g of 3,5-dibromo-2-methoxypyridine and 8.1 g of 2-tributyl stannyl pyridine was incorporated with 1.0 g of tetrakistriphenylphosphine palladium, followed by stirring at 120° C. for 2 hours in nitrogen atmosphere. After the mixture was returned to room temperature, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/hexane=1:3), to give 2.8 g of the title compound as a pale yellow powder.

Workup

  1. customwas returned to room temperature
  2. customthe solvent was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane=1:3)

Sources & evidence

ORD record
ord-253969ca3d7c48e0a221fdf052d80bba
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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