تفاعل #86913

معادلة التفاعل

4-amino-3-iodobenzonitrile

4-(triethylsilyl)but-3-yn-1-ol

lithium chloride

sodium carbonate

→

title compound

المردود 51.8%

3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

المردود 51.8%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe solution was filtered through celite
2. 2
   workup.ADDITIONdiluted in ethyl acetate
3. 3
   غسيلwashed with brine and sodium thiosulphate
4. 4
   أخرىdried
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane)

الإجراء التجريبي

4-amino-3-iodobenzonitrile (1.65 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.57 mL; 7.44 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.276 g; 0.338 mmol), lithium chloride (0.287 g; 6.76 mmol), sodium carbonate (1.43 g; 13.52 mmol) in DMF (14 mL) was stirred at 100° C. for 15 hours. The solution was filtered through celite, diluted in ethyl acetate, washed with brine and sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) to yield 0.873 g (43%) of the title compound as a yellow solid.

المصدر