900535-85-5

Usage

Structure

Thiopyridine derivative containing a phenylethynyl group and a methyl group

Usage

Building block in organic synthesis for the preparation of pharmaceuticals, agrochemicals, and materials

Biological activities

Potential antifungal and antitumor effects

Medicinal properties

Studied for its potential medicinal properties

Importance

Valuable intermediate in the production of diverse chemical compounds

Applications

Potential applications in pharmaceutical research and development

Upstream product

• 884863-17-6 2-bromo-3-(methylthio)pyridine 
• 536-74-3 phenylacetylene 
• 40273-45-8 2-bromo-3-fluoropyridine 
• 18794-33-7 3-methylsulfanylpyridine 

Relevant academic research and scientific papers

Regiocontrolled SNAr reaction on 2,3-dihalopyridines with NaSMe to obtain bromo(methylthio)pyridines as key precursors of 3-halo-2-(hetero) arylthieno[2,3- b ]pyridines and thieno[3,2- b ]pyridines

The synthesis of 3-halo-2-(hetero)arylthieno[2,3-b]pyridines and 3-halo-2-(hetero)arylthieno[3,2-b]pyridines has been performed through a three-step methodology from 3-bromo-2-chloropyridine or 2-bromo-3- fluoropyridine, respectively. The key step of this methodology is the formation of the required bromo(methylthio)pyridines by a regiocontrolled nucleophilic aromatic substitution (SNAr) with sodium methanethiolate (NaSMe). Then, the Sonogashira coupling with (hetero)arylalkynes followed by a halocyclization with bromine or iodine, afforded the expected 3-halo-2-(hetero)arylthienopyridines.

New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine

The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by