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

HRID 1943723
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HRID 1943723 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[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[N: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.[OH-].[Na+]>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[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[N:25][CH:24]=4)=[CH:22][C:14]2=3)=[O:12])[CH:5]=[C:6]([Br:10])[C:7]=1[OH:8]
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66936506(3,5-Dibromo-4-methoxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

생성물 1

HCID 44608709(3,5-Dibromo-4-hydroxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone수율 27.7%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

Under nitrogen atmosphere, in a 10 ml flask, (3,5-dibromo-4-methoxy-phenyl)-(7-isoquinolin-4-yl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (11.3 mg, 0.020 mmol) was dissolved in dichloromethane, and then cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (0.2 ml, 0.203 mmol) was added thereto and then stirred at room temperature for 18 hours. After adjusting to pH 6 with 1N NaOH solution, the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. Diethyl ether was added to the formed solid and stirred for 30 minutes and then filtered to obtain the target compound 61 as white solid (3.0 mg, 27%).

후처리

  1. temperaturecooled to 0□
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. additionDiethyl ether was added to the formed solid
  8. stirringstirred for 30 minutes
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-c0af605cf05c43fe9334219fcb3e5b39
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394792B2

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