Succinimide → HCID 119086895, compound

HRID 2206199Notes

Reaction equation

HRID 2206199 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].[H-].[Na+].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([B:18]([OH:20])[OH:19])=[CH:14][CH:13]=1>CN(C=O)C>[O:7]=[C:2]1[CH2:3][CH2:4][C:5](=[O:6])[N:1]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([B:18]([OH:20])[OH:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11439SuccinimideHCID 24758Sodium hydrideHCID 27355934-(Bromomethyl)phenylboronic acid

Product 1

HCID 119086895HCID 119086895, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (10 mL) of pyrrolidine-2,5-dione (500 mg) in DMF was added sodium hydride (60% dispersion in mineral oil, 252 mg) at 0° C., and the mixture was stirred for 1 hr. (4-(Bromomethyl)phenyl)boronic acid (903 mg) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and crystallized from ethyl acetate and diisopropyl ether to give the title compound (520 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customcrystallized from ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-57af2ed9fb994f989729249dda26c7bd
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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