反応 #86913

反応方程式

4-amino-3-iodobenzonitrile

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

lithium chloride

sodium carbonate

→

title compound

収率 51.8%

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

収率 51.8%

溶媒

DMF

反応条件

後処理

1. 1
   ろ過The solution was filtered through celite
2. 2
   workup.ADDITIONdiluted in ethyl acetate
3. 3
   洗浄washed with brine and sodium thiosulphate
4. 4
   その他dried
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane)

実験手順

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.

出典