反应详情

温度

150 °C

6-Dimethylamino-3,4-dihydro-2H-isoquinolin-1-one (762 mg, 4.01 mmol), cuprous iodide (153mg, 0.802 mmol) and potassium carbonate (554 mg, 4.01 mmol) were deposited in a sealed type vessel. 6 mL DMSO and 1,3-dibromobenzene (1.89 g, 8.01 mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 150° C. for 24 hours. Cuprous iodide (153 mg, 0.802 mmol) was added and the mixture was heated at 150° C. for an additional 24 hours. This was diluted with dichoromethane and filtered through a pad of celite. The filtrate was partitioned between dichloromethane and 5% aq. ammonium hydroxide. The dichloromethane layer was dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 25 to 100% ethyl acetate/hexanes) to yield 2-(3-Bromo-phenyl)-6-dimethylamino-3,4-dihydro-2H-isoquinolin-1-one (939 mg, 2.72 mmol). MS (ESI) 345.0 (M+H)+.

1. customArgon was bubbled through the mixture for 2 minutes
2. customthe lid was tightly closed
3. temperaturethe mixture was heated at 150° C. for an additional 24 hours
4. filtrationfiltered through a pad of celite
5. customThe filtrate was partitioned between dichloromethane and 5% aq. ammonium hydroxide
6. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated in vacuo
8. custompurified by flash chromatography (gradient elution 25 to 100% ethyl acetate/hexanes)