Sodium Acetate → 3-Phenoxypyridin-2-amine

HRID 1809544Notes

Reaction equation

HRID 1809544 reaction equation
C([O-])(=O)C.[Na+].Br[C:7]1[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:8]=1[O:9][C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=1.[H][H]>CCO.[OH-].[OH-].[Pd+2]>[O:9]([C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=1)[C:8]1[CH:7]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 674855643-(2,4-Dibromophenoxy)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 112176683-Phenoxypyridin-2-amineYield 71.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A 2 L Parr bottle was charged with sodium acetate (28.6 g, 349 mmol), 10% Pd(OH)2/C (5.0 g, 7.12 mmol) and 3-(2,4-dibromophenoxy)pyridin-2-amine (60 g, 174 mmol) in 1 L EtOH and placed under 35 psi hydrogen for 18 hours. The reaction was filtered through a plug of celite and then concentrated. The residue was redissolved in CH2Cl2 and washed with aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated. The dark residue was dissolved in EtOAc and charcoal added. The mixture was stirred for 30 minutes then filtered though a plug of celite. The crude material was triturated with 4:1 (EtOAc and hexanes) to afford 3-phenoxypyridin-2-amine (23.2 g, 71.4% yield).

Workup

  1. filtrationThe reaction was filtered through a plug of celite
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in CH2Cl2
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe dark residue was dissolved in EtOAc
  9. additioncharcoal added
  10. filtrationthen filtered though a plug of celite
  11. customThe crude material was triturated with 4:1 (EtOAc and hexanes)

Sources & evidence

ORD record
ord-433f3db328e349fab1dc7576e16e1659
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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