N,N'-Dimethylethylenediamine → HCID 67609006, compound

HRID 1467976Notes

Reaction equation

HRID 1467976 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([F:13])[F:12].[CH3:14][S:15]([O-:17])=[O:16].[Na+].CNCCNC>CS(C)=O>[F:12][C:5]1([F:13])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:3]=2)[NH:7][C:6]1=[O:11]

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 2733271Sodium methanesulfinateHCID 226077815-Bromo-3,3-difluoro-1,3-dihydro-indol-2-one

Product 1

HCID 67609006HCID 67609006, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 5-bromo-3,3-difluoroindolin-2-one (5.0 g, 20 mmol) in DMSO (50 mL), sodium methanesulfinate (3.0 g, 30 mmol), copper(I) trifluoromethane-sulfonate benzene complex (1.52 g, 3.022 mmol) and N,N′-dimethylethylenediamine (0.33 mL, 3.022 mmol) were added and stirred at 120° C. for 14 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and resulting residue was purified by flash column chromatography to give the title product (2.9 g, 58.2%); MS: 247.9 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated in vacuo
  4. customresulting residue
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-4dfb267ff81c4319a9c35b4b3add4a02
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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