Sodium hydride → 4-(3,5-dibromo-4-methoxy-benzoyl)-4H-pyrido[4,3-b][1,4]oxazin-3-one

HRID 1943717Notes

Reaction equation

HRID 1943717 reaction equation
[O:1]1[CH2:6][C:5](=[O:7])[NH:4][C:3]2[CH:8]=[N:9][CH:10]=[CH:11][C:2]1=2.[H-].[Na+].[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([Br:26])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19]>O>[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([Br:26])[C:23]=1[O:24][CH3:25])[C:18]([N:4]1[C:5](=[O:7])[CH2:6][O:1][C:2]2[CH:11]=[CH:10][N:9]=[CH:8][C:3]1=2)=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 144799002H,3H,4H-pyrido[4,3-b][1,4]oxazin-3-oneHCID 337796303,5-Dibromo-4-methoxybenzoyl chloride

Product 1

HCID 446087054-(3,5-dibromo-4-methoxy-benzoyl)-4H-pyrido[4,3-b][1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By the same method as in Example 56, 4H-pyrido[4,3-b][1,4]oxazin-3-one (200 mg, 1.33 mmol), sodium hydride (56 mg, 1.40 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (437 mg, 1.33 mmol) were reacted, and then water was added thereto and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of ethyl acetate:methanol=9:1. The fractions containing the product were collected and evaporated to obtain the target compound 57, i.e., 4-(3,5-dibromo-4-methoxy-benzoyl)-4H-pyrido[4,3-b][1,4]oxazin-3-one, as white solid (125 mg, 21%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of ethyl acetate
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-a06c766a8bf14540afe41740c3a61ff7
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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