Water → 7-bromo-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one

HRID 1527887Notes

Reaction equation

HRID 1527887 reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C1C(=O)N([Br:19])C(=O)C1.O>CN(C=O)C>[Br:19][C:10]1[CH:9]=[N:8][C:3]2[NH:4][C:5](=[O:7])[CH2:6][O:1][C:2]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-one

Product 1

HCID 159259837-bromo-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2H-pyrido[3,2-b][1,4]oxazin-3-one (0.75 g, 5 mmol) in DMF (18 mL) was slowly added NBS (1.07 g, 6 mmol) under N2. The mixture was stirred at rt for 16 h. HPLC indicated 75% conversion. More NBS (0.53 g, 3 mmol) was added and the mixture was stirred for another 24 h. Water (5 mL) was added and the reaction flask was chilled. The white solid which separated was filtered and washed with EtOAc, H2O, Et2O, and dried under vacuum in the presence of P2O5 and then used directly in the next step (687 mg, 60%).

Workup

  1. stirringthe mixture was stirred for another 24 h
  2. temperaturethe reaction flask was chilled
  3. customThe white solid which separated
  4. filtrationwas filtered
  5. washwashed with EtOAc, H2O, Et2O
  6. dry with materialdried under vacuum in the presence of P2O5

Sources & evidence

ORD record
ord-4f8809ff4734481483f2d98139dedaaa
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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