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

HRID 1098303Notes

Reaction equation

HRID 1098303 reaction equation
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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-67b4d56095544fbb9f9ec40df47c0987
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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