Reacción #44911

Ecuación de reacción

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

Rendimiento 76.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrohaving been degassed under argon for 15 min.
2. 2
   OtroThe tube was then sealed
3. 3
   TemperaturaThe reaction was then cooled
4. 4
   Filtraciónfiltered
5. 5
   ConcentraciónThe filtrate was concentrated under reduced pressure
6. 6
   Otrothe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

Procedimiento

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%).

Fuente