Water → N-[2-bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-2-cyanoquinoline-6-carboxamide

HRID 70812노트

반응식

HRID 70812 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([Br:12])([F:11])[F:10])[CH:5]=[C:4]([O:18][CH:19]([F:21])[F:20])[C:3]=1[NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N+:31]([O-])=[CH:30][CH:29]=[CH:28]2)=[O:24].[N:36]12CCCN=C1CCCC[CH2:37]2.O.C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([Br:12])([F:11])[F:10])[CH:5]=[C:4]([O:18][CH:19]([F:21])[F:20])[C:3]=1[NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[C:30]([C:37]#[N:36])[CH:29]=[CH:28]2)=[O:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86672968N-[2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-quinoline-6-carboxamide-1-oxide

생성물 1

HCID 49850069N-[2-bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-2-cyanoquinoline-6-carboxamide수율 36.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

N-[2-Bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-quinoline-6-carboxamide-1-oxide (0.41 g) was dissolved in tetrahydrofuran (50 ml), added with trimethylsilylnitrile (0.23 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.39 g), and stirred at 60° C. for 5 hours. Water was added to the reaction solution and extraction was carried out twice using ethyl acetate. The organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The resulting residues were purified by column chromatography to obtain N-[2-bromo-4-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)phenyl]-2-cyanoquinoline-6-carboxamide (0.15 g, 36%).

후처리

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  4. distillationthe solvent was distilled off under the reduced pressure
  5. customThe resulting residues were purified by column chromatography

출처 및 근거

ORD 기록
ord-2994b6482b384f5aa110eaa53f3e1efe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822691B2

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