Potassium Carbonate → 6-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

HRID 1054913Notes

Reaction equation

HRID 1054913 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[C:7]([NH2:13])=[N:8][C:9]([Br:12])=[CH:10][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Br:12][C:9]1[CH:10]=[CH:11][C:6]2[O:5][CH2:4][C:3](=[O:2])[NH:13][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 90011309HCID 90011309, compound

Product 1

HCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

(2-Amino-6-bromopyridin-3-yloxy)acetic acid methyl ester (4.0 g, 15 mmol) was dissolved in MeOH (40 mL). K2CO3 (3.0 g, 22 mmol) was added and the reaction was stirred at 70° C. for 1 hour. Then, the solvent was removed under reduced pressure and the resulting slurry was suspended in dichloromethane (DCM) and washed with H2O and then brine. The organic layer was dried (Na2SO4) and the product was precipitated from DCM/Et2O to give 6-bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one. Yield 1.9 g (8.3 mmol, 55%). LCMS (ESI): calc. C7H5BrN2O2=228, 230; obs. M+H=229, 231.

Workup

  1. customThen, the solvent was removed under reduced pressure
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe product was precipitated from DCM/Et2O

Sources & evidence

ORD record
ord-bea06c556a2b437e94b068a91e2a0763
Source dataset
uspto-grants-2016_07
Patent number
US09394315B2

Reaction notes

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