3-Cyanoindole

Chemical Properties

brown-grey to brown crystalline powder

Uses

Reactant for preparation of:

• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Inhibitors of the C-terminal domain of RNA polymerase II with antitumor activities
• 4-substituted β-lactams
• Biologically active Indoles
• Inhibitors of glycogen synthase kinase 3β (GSK-3)
• HIV-1 integrase inhibitors
• Indole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitors
• Aziridinomitosene skeleton
• Potential antiviral agents

Reactant for:

• Intramolecular oxidative C-H coupling reactions with applications in medium-ring synthesis techniques

Uses

3-Cyanoindole (cas# 5457-28-3) is a compound useful in organic synthesis.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 656, 1973
Tetrahedron, 50, p. 6549, 1994 DOI: 10.1016/S0040-4020(01)89685-X
Tetrahedron Letters, 18, p. 4417, 1977 DOI: 10.1016/S0040-4039(01)83524-3

General Description

3-Cyanoindole undergoes regiospecific bromination to afford 6-bromo-3-cyanoindole. 3-Cyanoindole is formed during the flash vacuum thermolysis (FVT) of 3-azidoquinoline.

Synthesis

A 3-cyanoindole compound synthesis method includes: firstly, taking indole compound, benzyl cyanide and CuI according to the molar ratio of 1:1-2:1-2, placing the indole compound, the benzyl cyanide and the CuI in a reaction vessel, and adding solvent into the reaction vessel until the indole compound and the benzyl cyanide are completely dissolved; then, placing the reaction vessel in oil bath at the temperature of 100-130°C with stirring for reaction for 30-34h, cooling to the room temperature, adding water as same as the solvent in volume, and extracting for 2-4 times by the aid of dichloromethane; and finally, separating using silica gel column chromatography prior to reduced pressure distillation so that the product, namely, the 3-cyanoindole compound is obtained.