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

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Reaction Steps

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.

Provenance & Evidence