N,N'-Dimethylethylenediamine → HCID 66920199, compound

HRID 1510084Notes

Reaction equation

HRID 1510084 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1>C(#N)C.[Cu]I>[F:25][C:26]1[CH:31]=[CH:30][C:29]([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[CH2:7][C:8]2=[O:12])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 27937496-Methoxyoxindole

Product 1

HCID 66920199HCID 66920199, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 6-methoxy-1,3-dihydro-indol-2-one (500 mg, 3.06 mmol), copper(I) iodide (58.3 mg, 306 μmol), N,N′-dimethylethylenediamine (65.3 μl, 613 μmol) and potassium carbonate (932 mg, 6.74 mmol) in ACN (7 ml) was added 4-fluoroiodobenzene (474 μl, 3.68 mmol). The reaction mixture was stirred for 3 h at 120° C. in a microwave reactor. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/HEP 1:4). 510 mg of the title compound were obtained.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (EA/HEP 1:4)

Sources & evidence

ORD record
ord-100aad503c8b41bfa6d760b1eec9071e
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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