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

HRID 7494

反応式

HRID 7494 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-125e886930dd4d1cb5902be4df9435c0
出典データセット
uspto-grants-2006_08
特許番号
US07087602B2

関連ノート

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