Water → HCID 66936483, compound

HRID 1943738Notes

Reaction equation

HRID 1943738 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[N:17][C:12]3[O:13][CH2:14][CH2:15][NH:16][C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1.[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([Br:31])[C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24].C(N(CC)CC)C.O>ClCCl>[Br:19][C:20]1[CH:21]=[C:22]([C:23]([N:16]2[CH2:15][CH2:14][O:13][C:12]3[N:17]=[CH:18][C:9]([C:5]4[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)=[CH:10][C:11]2=3)=[O:24])[CH:26]=[C:27]([Br:31])[C:28]=1[O:29][CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 66936957HCID 66936957, compound

Product 1

HCID 66936483HCID 66936483, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 7-(5-methoxy-pyridin-3-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (72 mg, 0.30 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (146 mg, 0.45 mmol) were dissolved in dichloromethane. Triethylamine (0.21 ml, 1.50 mmol) was added thereto and then stirred at room temperature for 3 hours. After completion of the reaction by adding water dropwise, the mixture was extracted with dichloromethane, and 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 amine silica eluting with a solvent of dichloromethane. The fractions containing the product were collected and evaporated to obtain (3,5-dibromo-4-methoxy-phenyl)-[7-(5-methoxy-pyridin-3-yl)-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl]-methanone as white solid (116 mg, 73%).

Workup

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

Sources & evidence

ORD record
ord-4bef920759784f8f9094b9c7cfe8a1da
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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