N-bromobutanimide → 2-Bromo-5-(3-chloro-2-fluoro-phenyl)-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204290Notes

Reaction equation

HRID 2204290 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]1[C:11]([F:36])=[C:12]([N:16]2[C:23](=[O:24])[C:22]3[CH:21]=[CH:20][N:19]([CH:25]([CH3:27])[CH3:26])[C:18]=3[CH:17]2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[CH3:35])[CH:13]=[CH:14][CH:15]=1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:8][C:20]1[N:19]([CH:25]([CH3:27])[CH3:26])[C:18]2[CH:17]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[CH3:35])[N:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([Cl:9])[C:11]=3[F:36])[C:23](=[O:24])[C:22]=2[CH:21]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 867030935-(3-chloro-2-fluoro-phenyl)-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Product 1

HCID 867030922-Bromo-5-(3-chloro-2-fluoro-phenyl)-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NBS (1.926 mmol) was added to a mixture of 5-(3-chloro-2-fluoro-phenyl)-6-(4-chloro-2-methyl-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Step A1) (1.965 mmol) in CCl4 (65 mL). After 1.5 h, the reaction mixture was diluted with EtOAc and successively washed with a saturated aqueous solution of NaHCO3, water and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid. tR: 5.69 min (HPLC 1); ESI-MS: tR=1.39 min, [M+H]+ 495/497/499 (LC-MS 1); TLC: Rf=0.12 (CH2Cl2).

Workup

  1. washsuccessively washed with a saturated aqueous solution of NaHCO3, water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-4090b389d522457f9e416a188aba0b11
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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