Water → HCID 66936798, compound

HRID 1943708Notes

Reaction equation

HRID 1943708 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:15]=[N:14][C:9]3[O:10][CH2:11][CH2:12][NH:13][C:8]=3[CH:7]=2)=[CH:2]1.[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([Br:28])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21].C(N(CC)CC)C.O>ClCCl>[Br:16][C:17]1[CH:18]=[C:19]([C:20]([N:13]2[CH2:12][CH2:11][O:10][C:9]3[N:14]=[CH:15][C:6]([C:3]4[CH:4]=[CH:5][O:1][CH:2]=4)=[CH:7][C:8]2=3)=[O:21])[CH:23]=[C:24]([Br:28])[C:25]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 66936637HCID 66936637, compound

Product 1

HCID 66936798HCID 66936798, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 5 ml flask, 7-furan-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (18 mg, 0.089 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (32.1 mg, 0.098 mmol) were dissolved in dichloromethane (1 ml). Triethylamine (0.037 ml, 0.267 mmol) was added thereto and then stirred at 0° C. 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 preparative TLC eluting a solvent of dichloromethane:methanol=20:1. Silica gels containing the product were eluted with dichloromethane and the solvent was evaporated to obtain (3,5-dibromo-4-methoxy-phenyl)-(7-furan-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone as white solid (40 mg, 91%).

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 preparative TLC
  7. washeluting a solvent of dichloromethane
  8. additionSilica gels containing the product
  9. washwere eluted with dichloromethane
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b3e57c1ef1db49feb7c8e5efc079e940
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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