5-Benzyloxy-2-fluoro-4-methylphenol → 4-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline

HRID 393600

반응식

HRID 393600 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([OH:38])[CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[K+]>CS(C)=O>[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([CH:37]=1)[O:38][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 219910495-Benzyloxy-2-fluoro-4-methylphenolHCID 222652574-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 226466314-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline수율 69%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
160 °C

실험 절차

4-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline (250 mg, 0.74 mmol) was added to a solution of 5-benzyloxy-2-fluoro-4-methylphenol (257 mg 1.1 mmol) and potassium t-butoxide (125 mg, 1.1 mmol) in DMSO (3 ml) and the mixture heated at 160° C. for 1.5 hours. The mixture was allowed to cool and was partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4), and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline (105 mg, 69%).

후처리

  1. temperatureto cool
  2. customwas partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/methanol (95/5)

출처 및 근거

ORD 기록
ord-5a38eee06c30427a9e107d76bcd0c311
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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