1H-Isoindole-1,3(2H)-dione, 2-ethenyl- → 2-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dione

To a degassed solution of 3-bromo-5-(trifluoromethyl)aniline (1.00 g, 4.17 mmol) and ACN (40 mL) was added Pd(OAc)2 (0.46 g, 0.20 mmol), bis(2-methylphenyl)(3-methylphenyl)phosphine (0.13 g, 0.40 mmol), and TEA (1.15 mL, 8.25 mmol). After stirring for 1 h, 2-vinyl-1H-isoindole-1,3(2H)-dione (0.72 g, 4.17 mmol) was added. The solution was heated at reflux for 20 h and then allowed to cool to rt and filtered through Celite. The filtrate was washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to yield the title compound as a yellow solid (0.90 g, 62%). LCMS: (FA) ES+ 333.2 (M+1).

1. temperatureThe solution was heated
2. temperatureat reflux for 20 h
3. filtrationfiltered through Celite
4. washThe filtrate was washed with water and brine
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by column chromatography

ORD-Eintrag

ord-e1014b56976441ba8293770571c906a3

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07652041B2