Phthalamide → 2-[3-(4-Fluoro-phenyl)-2-oxo-propyl]-isoindole-1,3-dione

HRID 1971828Notes

Reaction equation

HRID 1971828 reaction equation
Cl[CH2:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[K].[C:14]([NH2:25])(=[O:24])[C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:17](N)=[O:18]>CN(C=O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3](=[O:12])[CH2:2][N:25]2[C:14](=[O:24])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17]2=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6956PhthalamideHCID 5462222PotassiumHCID 135582931-Chloro-3-(4-fluorophenyl)propan-2-one

Product 1

HCID 581269722-[3-(4-Fluoro-phenyl)-2-oxo-propyl]-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of example 30 (85 mg, 0.45 mmol) in DMF (1 mL), under a nitrogen atmosphere, was added potassium salt of phthalamide (96 mg, 0.52 mmol). The resulting mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with a mixture of ice-water and filtered. The slightly pink solid was washed with water to give the titled compound as a white product (79 mg, 62% yield).

Workup

  1. customThe reaction mixture was quenched with a mixture of ice-water
  2. filtrationfiltered
  3. washThe slightly pink solid was washed with water

Sources & evidence

ORD record
ord-f77239f5007240efb09b250035a9010c
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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