4-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline → 4-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline

HRID 7494

반응식

HRID 7494 반응식
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[CH:11][C:12]([F:16])=[C:13]([OH:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[N:21][CH:20]=1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[CH:11][C:12]([F:16])=[C:13]([CH:14]=1)[O:15][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[N:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 107070484-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnolineHCID 219910495-Benzyloxy-2-fluoro-4-methylphenol

생성물 1

HCID 219910634-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline수율 53.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

The starting material, 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline was obtained by heating a solution of 5-benzyloxy-2-fluoro-4-methylphenol (314 mg, 1.3 mmol) and 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (280 mg, 1 mmol), (prepared as described for the starting material in Example 2), in pyridine (6 ml), at reflux for 15 hours. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water adjusted to pH7. The organic layer was separated, washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/ether (4/6 followed by 3/7) as eluent to give 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline as a white solid (247 mg, 53%).

후처리

  1. custom(prepared
  2. temperatureat reflux for 15 hours
  3. customAfter evaporation of the solvent
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialbrine, dried (MgSO4)
  8. customthe solvent evaporated
  9. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-125e886930dd4d1cb5902be4df9435c0
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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