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

HRID 393589노트

반응식

HRID 393589 반응식
C([O:8][C:9]1[C:10]([CH3:39])=[CH:11][C:12]([F:38])=[C:13]([CH:37]=1)[O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1)C1C=CC=CC=1>[Pd].CN(C=O)C.CO>[F:38][C:12]1[CH:11]=[C:10]([CH3:39])[C:9]([OH:8])=[CH:37][C:13]=1[O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 1

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

생성물 1

HCID 226465164-(2-Fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline수율 60.6%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline (274 mg, 0.5 mmol) and 10% palladium-on-charcoal catalyst (274 mg) in DMF (10 ml) and methanol (10 ml) was stirred under hydrogen at 5 atmospheres pressure for 3 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed by evaporation. The resulting solid was suspended in ether, collected by filtration and washed with methylene chloride and isopropanol to give 4-(2-fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(3-morpholinopropoxy)quinoline (134 mg, 25 60%).

후처리

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed by evaporation
  3. filtrationcollected by filtration
  4. washwashed with methylene chloride and isopropanol

출처 및 근거

ORD 기록
ord-a5e7f3b374bf48429129d6a2d2043894
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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