Water → {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}(5-isoxazolyl)methanone

HRID 228582

반응식

HRID 228582 반응식
Br[C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.C([Li])CCC.CCCCCC.[O:35]1[C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=[N:36]1.O>O1CCCC1>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=1[C:40]([C:39]1[O:35][N:36]=[CH:37][CH:38]=1)=[O:41]

참가 물질

6

반응물 4

HCID 962WaterHCID 2736707Isoxazole-5-carbonyl chlorideHCID 230783624-(2-Bromo-4-methylphenoxy)-6,7-dimethoxyquinolineHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 24879100{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}(5-isoxazolyl)methanone수율 26%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

4-(2-Bromo-4-methylphenoxy)-6,7-dimethoxyquinoline (100 mg) was dissolved in tetrahydrofuran (6 ml) to prepare a solution which was then cooled to −78° C. A 1.59 M n-butyllithium/hexane solution (0.4 ml) was added to the solution, and the mixture was stirred at −78° C. for 20 min. Isoxazole-5-carbonyl chloride (0.2 ml) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Further, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (27 mg, yield 26%).

후처리

  1. customto prepare a solution which
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-25a0a83dff7e4caa846058ecd1d22579
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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