Water → (7-Bromo-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-(3,5-dibromo-4-methoxy phenyl)-methanone

HRID 1943664Notes

Reaction equation

HRID 1943664 reaction equation
[Br:1][C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([Br:24])[C:21]=1[O:22][CH3:23])[C:16](Cl)=[O:17].C(N(CC)CC)C.O>ClCCl>[Br:1][C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][N:9]([C:16]([C:15]3[CH:19]=[C:20]([Br:24])[C:21]([O:22][CH3:23])=[C:13]([Br:12])[CH:14]=3)=[O:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 667890617-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

Product 1

HCID 66936520(7-Bromo-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-(3,5-dibromo-4-methoxy phenyl)-methanoneYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 ml flask, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (37 mg, 0.172 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (113 mg, 0.344 mmol) were dissolved in dichloromethane (0.5 ml). Triethylamine (0.120 ml, 0.860 mmol) was added thereto and then stirred at room temperature for 1 hour. After completion of the reaction by adding water to the reaction mixture, the organic layer was extracted with dichloromethane and the combined organic layer was washed with water and saturated saline solution, 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 dichloromethane:ethyl acetate:n-hexane=1:2:5. The fractions containing the product were collected and evaporated to obtain white solid (55 mg, 63%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe organic layer was extracted with dichloromethane
  3. washthe combined organic layer was washed with water and saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  8. additionThe fractions containing the product
  9. customwere collected
  10. customevaporated

Sources & evidence

ORD record
ord-894d1d2e05624fb6bbbb2cf5c474be0d
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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