N-bromobutanimide → 6-Bromo-3H-oxazolo(4,5-b)pyridin-2-one

HRID 1627540Notes

Reaction equation

HRID 1627540 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:10].[Br:11]N1C(=O)CCC1=O>C(#N)C.C(O)(=O)C>[Br:11][C:7]1[CH:8]=[C:9]2[O:1][C:2](=[O:10])[NH:3][C:4]2=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2799900Oxazolo(4,5-b)pyridin-2(3H)-one

Product 1

HCID 136144586-Bromo-3H-oxazolo(4,5-b)pyridin-2-oneYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3H-oxazolo[4,5-b]pyridin-2-one (13.6 g, 100 mmol) in acetonitrile (600 mL) and acetic acid (120 mL) was added N-bromosuccinimide (21.4 g, 120 mmol). The mixture was stirred at room temperature for 4 hr and the reaction was quenched with Na2S2O5 solution. After evaporation, the residue was partitioned between ethyl acetate and water. The organic layer was washed with 2N NaOH solution, brine, and dried over Na2SO4. The crude product was purified on a silica gel column to provide 6-bromo-3H-oxazolo[4,5-b]pyridin-2-one (11.5 g, 55% yield).

Workup

  1. customthe reaction was quenched with Na2S2O5 solution
  2. customAfter evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 2N NaOH solution, brine
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-2f28b75c4f5140b58e28222d9250343b
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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