HCID 4102537, compound → 5-bromo-2-isopropyl-2,3-dihydro-1H-isoindole

To a solution of 5-bromo-2-(1-methylethyl)-1H-isoindole-1,3(2H)-dione (Intermediate 5, 4.27 g) in tetrahydrofuran (THF) (100 mL) under nitrogen at room temperature was added 1.0M borane-tetrahydrofuran complex in THF (80 mL). The reaction mixture was heated at reflux for 48 hours. More 1.0M borane-THF complex in THF (50 mL) was added and the reaction mixture was heated at reflux for a further 24 hours. The reaction mixture was allowed to cool to room temperature. The reaction was quenched by the dropwise addition of 2N hydrochloric acid (80 mL). The reaction mixture was then heated at reflux for 1 hour. The reaction mixture was separated between ethyl acetate (300 mL) and water (50 mL). The organic phase was washed with 2N hydrochloric acid (100 mL). The combined aqueous phases were basified using 2N sodium hydroxide solution and then extracted with ethyl acetate (300 mL). This organic phase was washed with brine (100 mL) and dried over magnesium sulphate. The solvent was evaporated in vacuo to give the title compound (3.0 g) as a white solid.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 48 hours
3. temperaturethe reaction mixture was heated
4. temperatureat reflux for a further 24 hours
5. customThe reaction was quenched by the dropwise addition of 2N hydrochloric acid (80 mL)
6. temperatureThe reaction mixture was then heated
7. temperatureat reflux for 1 hour
8. customThe reaction mixture was separated between ethyl acetate (300 mL) and water (50 mL)
9. washThe organic phase was washed with 2N hydrochloric acid (100 mL)
10. extractionextracted with ethyl acetate (300 mL)
11. washThis organic phase was washed with brine (100 mL)
12. dry with materialdried over magnesium sulphate
13. customThe solvent was evaporated in vacuo

ORD record

ord-361e4335923b4720b05a8eabfabad017

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354539B2