Water → [3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol

HRID 228752

반응식

HRID 228752 반응식
I[C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[C:4]([CH3:23])[N:3]=1.CCCCCC.C([Li])CCC.[CH3:35][C:36]1[N:41]=[C:40]([CH:42]=[O:43])[CH:39]=[CH:38][CH:37]=1.O>O1CCCC1>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH3:22])[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:7]1[C:2]([CH:42]([C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([CH3:35])[N:41]=2)[OH:43])=[N:3][C:4]([CH3:23])=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 100936734-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline2회HCID 178418244HCID 178418244, 화합물

생성물 1

HCID 23078288[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol수율 73.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

4-(2-Iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxyquinoline (compound 116) (100 mg) was dissolved in tetrahydrofuran (7 ml) to prepare a solution which was then brought to −78° C. n-Butyllithium hexane solution (0.22 ml) was slowly added dropwise thereto, and the mixture was stirred at −78° C. for 20 min. 6-Methyl-2-pyridine-carbaldehyde (57 mg) was dissolved in tetrahydrofuran (7 ml) to prepare a solution which was then added dropwise to the reaction solution, followed by stirring at room temperature for 5 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give [3-(6,7-dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-(6-methyl-pyridin-2-yl)-methanol (73 mg, yield 73%).

후처리

  1. customto prepare a solution which
  2. customwas then brought to −78° C.
  3. additionwas slowly added dropwise
  4. customto prepare a solution which
  5. additionwas then added dropwise to the reaction solution
  6. stirringby stirring at room temperature for 5 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate layer was then washed with saturated brine
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. customThe solvent was removed by distillation under the reduced pressure
  11. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-0d51150efd0946e6bcbbdc7952f139f4
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

연결된 노트

불러오는 중…