Water → HCID 28492488, compound

HRID 2096998Notes

Reaction equation

HRID 2096998 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[NH:6]2.[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[N:6]2[CH2:18][C:17]1[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 45000124-Bromoisatin

Product 1

HCID 28492488HCID 28492488, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-bromoindoline-2,3-dione (200 mg, 0.89 mmol) in 5 ml DMF was added 4-Fluorobenzylbromide (0.120 ml, 0.98 mmol) then add NaH (35 mg, 0.89 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 270 mg (90%) of product.

Workup

  1. extractionextract three times with EtOAc
  2. washPool all organics and wash one time with brine
  3. dry with materialthen dry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate to dryness
  6. customThe residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50)

Sources & evidence

ORD record
ord-e6864e725592439b9f891b9cdea8733c
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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