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

HRID 1994109Notes

Reaction equation

HRID 1994109 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:12]=[CH:13]/[N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1>CCO.C1COCC1.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

5

Reactant 1

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

Product 1

HCID 591349662-[2-[3-Amino-5-(trifluoromethyl)phenyl]ethyl]-1h-isoindole-1,3(2h)-dioneYield 41%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C (10% by wt, 0.090 g) was added to a degassed solution of 2-{(E)-2-[3-amino-5-(trifluoromethyl)phenyl]vinyl}-1H-isoindole-1,3(2H)-dione (0.900 g, 2.71 mmol) in EtOH (56 mL) and THF (40 mL). The mixture was hydrogenated (50 psi) at rt until LC/MS indicated reaction was complete. The mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column chromatography (SiO2, 1:1 EtOAc:hexanes) to afford the desired product as a white solid (0.371 g, 40%). LCMS: (FA) ES+ 335.3 (M+1).

Workup

  1. customat rt
  2. customreaction
  3. filtrationThe mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (SiO2, 1:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-e333d2b5f1fc48118bb01b5e8843e5a2
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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