1H-Isoindole-1,3(2H)-dione, 2-ethenyl- → 2-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dione
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=C(C)C=1.[CH:35]([N:37]1[C:45](=[O:46])[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]1=[O:47])=[CH2:36]>CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)C>[NH2:5][C:4]1[CH:3]=[C:2](/[CH:36]=[CH:35]/[N:37]2[C:38](=[O:47])[C:39]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:45]2=[O:46])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- temperatureThe solution was heated
- temperatureat reflux for 20 h
- filtrationfiltered through Celite
- washThe filtrate was washed with water and brine
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-e1014b56976441ba8293770571c906a3
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652041B2
Reaction notes
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