Reaction #86913

Reaction equation

4-amino-3-iodobenzonitrile

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

lithium chloride

sodium carbonate

→

title compound

Yield 51.8%

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

Yield 51.8%

Solvents

DMF

Conditions

Workup

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

Procedure

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.

Source