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

3-Bromo-5-(trifluoromethyl)aniline (5.00 g, 0.0208 mol) was dissolved in AcCN (200 mL) and the solution was degassed with N2. Pd(OAc)2 (230 mg, 1.02 mmol), tris(2-methylphenyl)phosphine (630 mg, 2.07 mmol), and Et3N (5.75 mL, 0.041 mol) were added and the bright orange solution was allowed to stir at rt for 1 h. To this solution was added 2-vinyl-1H-isoindole-1,3(2H)-dione (3.61 g, 0.021 mol) and the reaction mixture was degassed and heated at reflux for 16 h. The reaction was filtered through Celite. The filtrate was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dione (1.99 g, 24% yield). LCMS: (FA) ES+ 334.

1. customthe solution was degassed with N2
2. customthe reaction mixture was degassed
3. temperatureheated
4. temperatureat reflux for 16 h
5. filtrationThe reaction was filtered through Celite
6. washThe filtrate was washed with water and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by column chromatography

ORD record

ord-79106a2bcccd4829a711477cc07df78d

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110687B2