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

HRID 1943653노트

반응식

HRID 1943653 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[N:19]=[CH:20][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[O:8]C.B(Br)(Br)Br.O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([N:13]2[CH2:18][CH2:17][O:16][C:15]3[N:19]=[CH:20][C:21]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 66936674(3,5-Dibromo-4-methoxy-phenyl)-(7-phenyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

생성물 1

HCID 44608066(3,5-Dibromo-4-hydroxy-phenyl)-(7-phenyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a 5 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-phenyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (14 mg, 0.03 mmol) was dissolved in dichloromethane and then cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (0.17 ml, 0.17 mmol) was added and then stirred at 0□ for 15 hours. After completion of the reaction, water was added thereto and the mixture was extracted with ethyl acetate 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 silica eluting with a solvent of dichloromethane:methanol=40:1. The fractions containing the product were collected and evaporated to obtain the target compound 20 as white solid (8.7 mg, 64%).

후처리

  1. temperaturecooled to 0□
  2. additionwas added
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  9. additionThe fractions containing the product
  10. customwere collected
  11. customevaporated

출처 및 근거

ORD 기록
ord-d0d5cf0ea1784937973eb75cdcd4f0f4
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

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