Water → HCID 66936666, compound

HRID 1943741Notes

Reaction equation

HRID 1943741 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:19]=[N:18][C:13]4[O:14][CH2:15][CH2:16][NH:17][C:12]=4[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Br:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([Br:32])[C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25].C(N(CC)CC)C.O>ClCCl>[Br:20][C:21]1[CH:22]=[C:23]([C:24]([N:17]2[CH2:16][CH2:15][O:14][C:13]3[N:18]=[CH:19][C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[C:9]5[C:4]=4[CH:3]=[CH:2][NH:1]5)=[CH:11][C:12]2=3)=[O:25])[CH:27]=[C:28]([Br:32])[C:29]=1[O:30][CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 66936733HCID 66936733, compound

Product 1

HCID 66936666HCID 66936666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 7-(1H-indol-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (130 mg, 0.52 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (204 mg, 0.62 mmol) were dissolved in dichloromethane. Triethylamine (0.36 ml, 2.59 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-(1H-indol-4-yl)-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl]-methanone as white solid (129 mg, 64% in two steps).

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-011b75af29594c3ea5b0e3defae5c464
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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