Reaktion #44911

Reaktionsgleichung

2-iodo-benzene

potassium phosphate

5-benzyloxy-2-methyl-1H-indole-3-carboxylic acid, ethyl ester

Compound 53

5-benzyloxy-2-methyl-1H-indole-3-carboxylic acid, ethyl ester

N,N′-dimethylethylenediamine

→

5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, ethyl ester

Ausbeute 76.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigehaving been degassed under argon for 15 min.
2. 2
   SonstigeThe tube was then sealed
3. 3
   TemperaturThe reaction was then cooled
4. 4
   Filtrationfiltered
5. 5
   EinengenThe filtrate was concentrated under reduced pressure
6. 6
   Sonstigethe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

Vorschrift

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%).

Quelle