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

HRID 1994108
Notes
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Reaction equation

HRID 1994108 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 15771086Bis(2-methylphenyl)(3-methylphenyl)phosphine

Product 1

HCID 591349702-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dioneYield 65%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 6342AcetonitrileSolvent

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

  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

Sources & evidence

ORD record
ord-e1014b56976441ba8293770571c906a3
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652041B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes