Water → 7-methylamino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one
Reaction equation
Br[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.C([O-])(=O)C.[Cs+].[CH3:28][NH2:29].CO.O>CN(C)C=O.[Cu](I)I>[CH3:28][NH:29][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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
30 mg (0.08 mmol) of the 7-bromo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one prepared in Step A, 18.6 mg (0.098 mmol) of copper iodide (I), and 39.1 mg (0.204 mmol) of cesium acetate were suspended in 0.5 ml of dry dimethylformamide. Thereafter, 200 μl of a 40% methylamine-methanol solution was added to the suspension, and the obtained mixture was then stirred at 100° C. overnight. Thereafter, water was added to the reaction solution, and the mixture was then extracted with methylene chloride. The extract was washed with a saturated saline solution, and was then dried over anhydrous magnesium sulfate. The extract was concentrated. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1), so as to obtain 15.4 mg (61%) of 7-methylamino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one.
Workup
- extractionthe mixture was then extracted with methylene chloride
- washThe extract was washed with a saturated saline solution
- dry with materialwas then dried over anhydrous magnesium sulfate
- concentrationThe extract was concentrated
- customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1)
Sources & evidence
- ORD record
- ord-49dbf85cff91409499ed809683e5d92e
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143274B2
Reaction notes
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