N,N'-Dimethylethylenediamine → HCID 58944725, compound

HRID 16633Notes

Reaction equation

HRID 16633 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[C:12]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]([CH3:18])=[C:12]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 6128625-Benzyloxy-3-ethoxycarbonyl-2-methylindole2×

Product 1

HCID 58944725HCID 58944725, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 5-benzyloxy-2-methyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 53, 0.14 g, 0.45 mmol) in toluene (6 ml) having been degassed under argon for 15 min. was added 2-iodo-benzene (0.10 ml, 0.48 g, 0.88 mmol), potassium phosphate (0.20 g, 0.94 mmol), copper (I) iodide (24 mg, 0.13 mmol), and then N,N′-dimethylethylenediamine (12 mg, 0.14 mmol) with continued degassing. The tube was then sealed and mixture was heated at 140° C. for 24 h. The reaction was then cooled and filtered. The filtrate was concentrated under reduced pressure and the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes) to yield 5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 54) as an orange oil (0.13 g, 76%).

Workup

  1. customhaving been degassed under argon for 15 min.
  2. customThe tube was then sealed
  3. temperatureThe reaction was then cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-910a907363b942c98278b766589d86c5
Source dataset
uspto-grants-2010_06
Patent number
US07737173B2

Reaction notes

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