2-(1H-indol-2-yl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (809 mg) in tetrahydrofuran (20 ml) at -30° C. under nitrogen atmosphere was added 1.64M butyllithium in hexane (5.33 ml). After being stirred at the same temperature for 30 minutes, the mixture was treated with a solution of indol-2-yl-acetonitrile (1.25 g) in tetrahydrofuran (10 ml) at -60° C. over 15 minutes. The mixture was stirred at the same temperature for an hour, and a solution of methyl iodide (1.14 g) in tetrahydrofuran (10 ml) was added dropwise over an hour. After the mixture was stirred at -60° C. for one hour and at ambient temperature for 2 hours, it was diluted with chilled water, and extracted two times with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by alumina column chromatography (10% ethylacetate-toluene) to give 2-(indol-2-yl)-2-methylpropiononitrile (354 mg). The mixture was stirred at the same temperature for an hour After the mixture was stirred at -60° C. for one hour and at ambient temperature for 2 hours extracted two times with ethyl acetate The organic layer was washed with brine dried over magnesium sulfate evaporated in vacuo The residue was purified by alumina column chromatography (10% ethylacetate-toluene)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diisopropylamine (809 mg) in tetrahydrofuran (20 ml) at -30° C. under nitrogen atmosphere was added 1.64M butyllithium in hexane (5.33 ml). After being stirred at the same temperature for 30 minutes, the mixture was treated with a solution of indol-2-yl-acetonitrile (1.25 g) in tetrahydrofuran (10 ml) at -60° C. over 15 minutes. The mixture was stirred at the same temperature for an hour, and a solution of methyl iodide (1.14 g) in tetrahydrofuran (10 ml) was added dropwise over an hour. After the mixture was stirred at -60° C. for one hour and at ambient temperature for 2 hours, it was diluted with chilled water, and extracted two times with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by alumina column chromatography (10% ethylacetate-toluene) to give 2-(indol-2-yl)-2-methylpropiononitrile (354 mg). The mixture was stirred at the same temperature for an hour After the mixture was stirred at -60° C. for one hour and at ambient temperature for 2 hours extracted two times with ethyl acetate The organic layer was washed with brine dried over magnesium sulfate evaporated in vacuo The residue was purified by alumina column chromatography (10% ethylacetate-toluene)