Potassium Carbonate → 4-Chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline

HRID 7491ノート

反応式

HRID 7491 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[N:18][CH:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:8][C:9]3[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=3)=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[N:18][CH:17]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 7365362-(chloromethyl)-1-methyl-1H-imidazoleHCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

生成物 1

HCID 219910194-Chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline収率 29%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for the starting material in Example 10), in DMF (6 ml). After stirring overnight at 40° C. the mixture was diluted with water and adjusted to pH7. After extraction with ethyl acetate the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/methanol (98/2) as eluent to give 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (111 mg, 29%).

後処理

  1. custom(prepared
  2. extractionAfter extraction with ethyl acetate the organic layer
  3. washwas washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-a2793211692d4541affe62f1da13a23a
出典データセット
uspto-grants-2006_08
特許番号
US07087602B2

反応ノート

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