Imidazole → 7-imidazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1098303ノート

反応式

HRID 1098303 の反応式
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.[Cl-].[NH4+]>O1CCOCC1.[Cu](I)I>[N:23]1([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]3=[O:12])=[CH:4][CH:3]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

参加物

8

反応物 5

HCID 795ImidazoleHCID 8070N,N'-DimethylethylenediamineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 231568037-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 231567797-imidazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one収率 93.4%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

10.4 mg (0.025 mmol) of the 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Step A, 0.48 mg (0.0025 mmol) of copper iodide (I), 2.0 mg (0.03 mmol) of imidazole, and 11.1 mg (0.0525 mmol) of potassium phosphate were suspended in 0.25 ml of 1,4-dioxane. Then, 2.6 μl of N,N′-dimethylethylenediamine was added to the suspension, and the obtained mixture was then stirred at 110° C. overnight. Thereafter, the reaction solution was cooled to a room temperature, and a saturated ammonium chloride aqueous solution was then added to the reaction solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and was then concentrated. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=25:1 to 20:1), so as to obtain 8.3 mg (93%) of 7-imidazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless viscous oily substance.

後処理

  1. temperatureThereafter, the reaction solution was cooled to a room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationwas then concentrated
  5. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=25:1 to 20:1)

出典と根拠

ORDレコード
ord-67b4d56095544fbb9f9ec40df47c0987
出典データセット
uspto-grants-2012_03
特許番号
US08143274B2

反応ノート

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