Ethyl Acetate → 8-vinyl-3,4-dihydro-1H-1-benzazepine-2,5-dione

Temperature

100 °C

To a degassed solution of 8-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (0.3 g, 1.0 mmol) in DMF (5 mL) was added CuI (19 mg, 0.1 mmol), KF (116 mg, 2.0 mmol), tributylethenylstannane (0.58 mL, 2.0 mmol), and Pd(PPh3)4 (116 mg, 0.1 mmol). The reaction mixture was allowed to stir at 100° C. for 4 h. After being allowed to cool to rt, EtOAc (50 mL) and a 1M aqueous KF solution (25 mL) were added and the mixture was allowed to stir for an additional 40 min. The mixture was filtered over Celite® and the organic solution was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was treated with n-pentane and filtered. The resulting solid was purified by column chromatography to provide 8-vinyl-3,4-dihydro-1H-1-benzazepine-2,5-dione (80 mg, 40%).

1. temperatureto cool to rt
2. stirringto stir for an additional 40 min
3. filtrationThe mixture was filtered over Celite®
4. customthe organic solution was separated
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. additionThe residue was treated with n-pentane
10. filtrationfiltered
11. customThe resulting solid was purified by column chromatography

ORD record

ord-39fb4b9a21d54ea0867b6436f8073f72

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998952B2