900152-50-3

Upstream product

• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 900152-44-5 5-(3-hydroxy-4-methoxy-phenyl)-1-(4-methoxy-benzyl)-4-(3,4,5-trimethoxy-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 900152-42-3 4-(3-hydroxy-4-methoxy-phenyl)-1-(4-methoxy-benzyl)-5-(3,4,5-trimethoxy-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 900152-46-7 4-benzo[1,3]dioxol-5-yl-5-(3-hydroxy-4-methoxy-phenyl)-1-(4-methoxy-benzyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 900152-51-4 methyl 4,5-dibromo-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate 

Relevant academic research and scientific papers

Successive Pd-Catalyzed Decarboxylative Cross-Couplings for the Modular Synthesis of Non-Symmetric Di-Aryl-Substituted Thiophenes

Oligothiophenes are important organic molecules in a number of burgeoning industries as semi-conducting materials due to their extensive π-conjugation and charge transport properties. Typically, non-symmetric, di-aryl-substituted thiophenes are prepared by the successive formation of Grignards, organotin, and/or boronic acid intermediates that can be subsequently employed in cross-coupling reactions. While reliable, these approaches present synthetic difficulties due to the reactivity of organo-metallic/pseudo-metallic species, and produce considerable amounts of waste due to necessary pre-functionalization. We have developed a decarboxylative cross-coupling route as an effective strategy for the modular and less wasteful synthesis of a wide range of non-symmetric, di-arylthiophenes. This method uses a thiophene ester building block for successive decarboxylative palladium-catalyzed couplings that allows for the efficient synthesis and evaluation of the opto-electronic properties of a library of candidate semi-conductors with functional groups that could be challenging to access using previous routes.

Structural Optimizations of Thieno[3,2-b]pyrrole Derivatives for the Development of Metabolically Stable Inhibitors of Chikungunya Virus

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus, and there is no approved effective antiviral treatment currently available for CHIKV. We previously reported the discovery of thieno[3,2-b]pyrrole 1b that displayed good antiviral activit

4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: Synthesis and evaluation as anti-mitotic and cytotoxic agents

The 4,5-diarylated-1H-pyrrole-2-carboxylates 3-8 have each been prepared as hybrids of the potent anti-mitotic agent combretastatin A-4 (1) and the similarly active marine alkaloid lamellarin T (2). The key steps involved selective lithium-for-halogen exchange at C5 within the N-PMB protected 4,5-dibromopyrrole 22 and Negishi cross-coupling of the derived zincated species with the relevant aryl iodide. The ensuing 5-aryl-4-bromopyrrole then engaged in Suzuki-Miyaura cross-coupling with the appropriate arylboronic acid to give the 4,5-diarylated pyrroles 4, 6 and 8. TFA-promoted removal of the N-PMB group within these last compounds then gave the N-unsubstituted congeners 3, 5 and 7. Compounds 3-8 have all been evaluated for their anti-mitotic and cytotoxic properties and two of them, 3 and 5, display useful activities although they are less potent than combretastatin A-4. Crown Copyright