Water → 1-{4-[1-(3,5-dibromo-4-methoxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-phenyl}-ethanone

HRID 1943735노트

반응식

HRID 1943735 반응식
[NH:1]1[CH2:6][CH2:5][O:4][C:3]2[N:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:10][C:2]1=2.[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]([CH:27]=[C:28]([Br:32])[C:29]=1[O:30][CH3:31])[C:24]([N:1]1[CH2:6][CH2:5][O:4][C:3]2[N:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:10][C:2]1=2)=[O:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 669366261-[4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-phenyl]-ethanone

생성물 1

HCID 669361501-{4-[1-(3,5-dibromo-4-methoxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-phenyl}-ethanone수율 94.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 10 ml flask, 1-[4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-phenyl]-ethanone (59 mg, 0.23 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (287 mg, 0.87 mmol) were dissolved in dichloromethane. Triethylamine (0.32 ml, 2.3 mmol) was added thereto and then stirred at room temperature for 12 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 1-{4-[1-(3,5-dibromo-4-methoxy-benzoyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl]-phenyl}-ethanone as white solid (119 mg, 94%).

후처리

  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

출처 및 근거

ORD 기록
ord-d1d1bc0f5188493f8badec1006c34606
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

반응 노트

불러오는 중…