4-Acetoxyindole

Description

4-acetoxylindole is also known as 4-Indolyl acetate. It can be used as standards of the reverse phase HPLC during separation of small molecules. It can also be used as reactant during the preparation of inhibitors of HIV-attachment, prostanoid EP3 antagonist, indolyl-nitroalkanes and psilocybin.

Uses

Reactant for preparation of:

• Inhibitors of HIV-1 attachment
• Prostanoid EP3 receptor antagonist, as a novel antiplatelet agent
• Indolyl-nitroalkanes via N-bromosuccinimide catalyzed synthesis
• Psilocybin as a medicinal agent

Uses

4-Acetoxyindole is a useful intermediate for organic synthesis of Psilocine and Psilocine analogs.

Application

In addition to its pharmaceutical applications, 4-Acetoxyindole is also employed in the synthesis of functional materials and organic electronics. Its distinctive properties enable it to be used in the development of dyes and pigments, enhancing the performance of various industrial products.

General Description

4-Acetoxyindole is a chromophore that belongs to the pyrrole family of compounds. It has been shown to react with an ionic liquid under acidic conditions to form a protonated intermediate, which can be deprotonated by a nucleophile. This reaction yields an acetate anion and a fluorescing product. 4-Acetoxyindole also reacts with deuterium gas, yielding an acetate, a deuterium atom, and fluorescing product. The reaction is reversible and the yield of the product depends on the concentration of the reactants. 4-Acetoxyindole has strong carbonyl groups that make it reactive towards other functional groups. These reactions are useful for synthesizing heterocycles such as indoles and isoquinolines.

Synthesis

4-Hydroxyindole (1 eq. of limiting reagent) was loaded into the vessel under N2, followed by DCM (dichloromethane; based on the loading of 4-hydroxyindole, 6 v/v). The reaction was cooled to 0-5 ??C and pyridine (1.2 eq.) was added dropwise at 0-5 ??C. Acetic anhydride (1.1 eq.) was added dropwise at 0-5??C and the reaction was warmed to 20??C-25??C for 1-1.5 hr and stirred at 20??C-25??C for an additional 3 hr. The reaction was sampled and analyzed for completion. The reaction was then washed three times with 20% aqueous citric acid solution (based on 4-hydroxyindole loading, 3x 3 volume) and once with saturated NaHCO3 (based on 4-hydroxyindole loading, 3 volume). The DCM solution was dried over MgSO4 and filtered, and the DCM layer was concentrated to half volume by distillation. Heptane (based on 4-hydroxyindole loading, 6 volumes) was added and additional DCM was removed by distillation until complete precipitation of stage 1 occurred. The reaction was cooled to 15 ??C - 25 ??C and the solid was collected by filtration, washed with heptane (based on 4-hydroxyindole loading, 1 volume) and dried under vacuum at 60 ??C overnight to give 4-acetoxyindole.

References

http://www.sigmaaldrich.com/catalog/product/aldrich/259047?lang=en&region=US
https://pubchem.ncbi.nlm.nih.gov/compound/4-Acetoxyindole