تفاعل #44911

معادلة التفاعل

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

المردود 76.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىhaving been degassed under argon for 15 min.
2. 2
   أخرىThe tube was then sealed
3. 3
   درجة الحرارةThe reaction was then cooled
4. 4
   ترشيحfiltered
5. 5
   تركيزThe filtrate was concentrated under reduced pressure
6. 6
   أخرىthe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

الإجراء التجريبي

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%).

المصدر