反应详情

0.5 g of methyl benzyl[2-(2-bromophenyl)ethyl]carbamate is dissolved under an inert atmosphere in 20 cm3 of dichloromethane at a temperature close to 20° C. 0.526 g of N,N-dimethylpyridin-4-amine is added, then the reaction mixture is cooled to a temperature close to 0° C. 1.2 cm3 of trifluoromethanesulfonic anhydride is introduced dropwise. The suspension obtained is stirred for 15 min at a temperature close to 0° C., then for 4 h 30 min while allowing it to gradually climb back up to a temperature close to 20° C. Dichloromethane is added to the reaction mixture and also a saturated aqueous solution of ammonium chloride. The aqueous phase is extracted with dichloromethane. The organic phases are combined, dried over magnesium sulfate then concentrated using a rotary evaporator under reduced pressure (5 kPa). The crude product obtained (1 g) is purified by flash chromatography over silica (column: 90 g; particle size: 15-40 μm; eluent: 100% dichloromethane to 95% dichloromethane/5% ethyl acetate gradient). After concentrating the fractions under reduced pressure, 0.22 g of 2-benzyl-5-bromo-3,4-dihydroisoquinolin-1(2 H)-one is obtained.

1. customclose to 20° C
2. temperaturethe reaction mixture is cooled to a temperature
3. customclose to 0° C
4. customThe suspension obtained
5. customclose to 0° C.
6. waitfor 4 h 30 min while allowing
7. customclose to 20° C
8. extractionThe aqueous phase is extracted with dichloromethane
9. dry with materialdried over magnesium sulfate
10. concentrationthen concentrated
11. customa rotary evaporator under reduced pressure (5 kPa)
12. customThe crude product obtained (1 g)
13. customis purified by flash chromatography over silica (column: 90 g; particle size: 15-40 μm; eluent: 100% dichloromethane to 95% dichloromethane/5% ethyl acetate gradient)
14. concentrationAfter concentrating the fractions under reduced pressure