Synthesis of (Z)-5-[(5-(2-(phenylsulfonyl-ethyl)-1H-indol-3-yl)methylene]thiazolidine-2,4-dione of potential pharmacological interest was written by Laxminarayana, Keetha;Rajendiran, Chinnapillai;Mukkanti, Khagga. And the article was included in Asian Journal of Chemistry in 2013.HPLC of Formula: 10102-94-0 This article mentions the following:
Formylation of 5-bromo-1H-indole under Vilsmeier-Hack formylation conditions using POCl3 and DMF as a reagents under cooling conditions (0-5掳) followed by a simple process gave 5-bromo-1H-indole-3-carboxaldehyde. A condensation reaction of this aldehyde with 2,4-thiazolidinedione in toluene as a solvent in the presence of PTSA and TBAB as a phase transfer catalyst under stirring at room temperature for 10-30 min, then slowly raising the temperature to 105掳 and maintaining for 12-15 h gave (Z)-5-[(5-bromo-1-alkyl-1H-indol-3-yl)methylene]-2,4-thiazolidinedione. Further condensation of this intermediate with phenyl(vinyl)sulfone in the presence of palladium acetate as a catalyst and DMF as a solvent and heating to 100-105掳 for 16 h gave (5Z)-5-[1-alkyl-5-[(E)-2-[(phenylsulfonyl)vinyl]-1H-indol-3-yl]methylene]-2,4-thiazolidinedione derivatives Reduction of this compound in the presence of hydrogen gas, palladium-carbon as a catalyst in acetic acid medium and methanol as a solvent heating at 45-50掳 for 8 h gave (Z)-5-[1-alkyl-5-[2-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl]methylene]-2,4-thiazolidinedione derivatives These products could also be prepared by an alternate route and the products were characterized on the basis of spectral and anal. data. The title compounds thus formed included a thiazolidinedione indole sulfone (I). In the experiment, the researchers used many compounds, for example, 5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0HPLC of Formula: 10102-94-0).
5-Bromo-1-methyl-1H-indole-3-carbaldehyde (cas: 10102-94-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 10102-94-0
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles