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

HRID 1943705노트

반응식

HRID 1943705 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[N:15][C:10]3[O:11][CH2:12][CH2:13][NH:14][C:9]=3[CH:8]=2)[CH:2]=1.[Br:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([Br:29])[C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22].C(N(CC)CC)C.O>ClCCl>[Br:17][C:18]1[CH:19]=[C:20]([C:21]([N:14]2[CH2:13][CH2:12][O:11][C:10]3[N:15]=[CH:16][C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[CH:8][C:9]2=3)=[O:22])[CH:24]=[C:25]([Br:29])[C:26]=1[O:27][CH3:28]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 669368927-pyridin-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

생성물 1

HCID 66936151(3,5-Dibromo-4-methoxy-phenyl)-(7-pyridin-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone수율 49.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 10 ml flask, 7-pyridin-3-yl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (30 mg, 0.140 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (50.5 mg, 0.154 mmol) were dissolved in dichloromethane (2 ml). Triethylamine (0.058 ml, 0.42 mmol) was added thereto and then stirred at room temperature for 1 hour. 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 ethyl acetate: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-pyridin-3-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone as white solid (35 mg, 49%).

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

출처 및 근거

ORD 기록
ord-623d5f6467e6433abe8b255d89a6b95a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

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