反応 #44911

反応方程式

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

収率 76.0%

溶媒

toluene

反応条件

後処理

1. 1
   その他having been degassed under argon for 15 min.
2. 2
   その他The tube was then sealed
3. 3
   温度The reaction was then cooled
4. 4
   ろ過filtered
5. 5
   濃縮The filtrate was concentrated under reduced pressure
6. 6
   その他the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)

実験手順

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%).

出典