1H-Isoindole-1,3(2H)-dione, 2-ethenyl- → HCID 53900851, compound

HRID 890821Notes

Reaction equation

HRID 890821 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:16]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[CH2:17].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:17]=[CH:16][N:18]1[C:19](=[O:28])[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 53936336Tert-butyl 2-(3-bromophenyl)acetate

Product 1

HCID 53900851HCID 53900851, compoundYield 25.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-phenyl acetic acid tert-butyl ester (5.64 g, 20.80 mmol), N-vinyl phthalimide (3.60 g, 20.80 mmol), diisopropylethylamine (3.63 g, 28.08 mmol), palladium acetate (107 mg, 0.478 mmol), and tri-o-tolylphosphine (475 mg, 1.56 mmol) in acetonitrile (10 mL) was stirred at 90° C. for 20 h. The reaction was cooled to room temperature and ice water (50 mL) was added. EtOAc (50 mL) was added and the organic solution was washed with 5.5% HCl followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 9:1 to 4:1) provided the title compound (1.95 g). MS 381 (M+18).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washthe organic solution was washed with 5.5% HCl
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (hexanes:EtOAc 9:1 to 4:1)

Sources & evidence

ORD record
ord-a5cc08aa49c54c228d56be16cb867e2a
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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