반응 #44911

반응 방정식

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

수율 76.0%

용매

toluene

반응 조건

후처리

1. 1
   기타having been degassed under argon for 15 min.
2. 2
   기타The tube was then sealed
3. 3
   온도The reaction was then cooled
4. 4
   여과filtered
5. 5
   농축The filtrate was concentrated under reduced pressure
6. 6
   기타the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

실험 절차

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%).

출처