N,N'-Dimethylethylenediamine → HCID 12777166, compound

HRID 1510064Notes

Reaction equation

HRID 1510064 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+].I[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C.[Cu]I>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[N:9]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 27937496-Methoxyoxindole

Product 1

HCID 12777166HCID 12777166, compoundYield 75.1%

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-dihydroindol-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 (6.5 ml) was added iodobenzene (411 μl, 3.68 mmol). The reaction mixture was stirred for 1 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 1:5). 550 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 1:5)

Sources & evidence

ORD record
ord-58cd0d1ff38f497b8c697d73fe373b2f
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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