127572-59-2

Basic information

• Product Name: 1H-Pyrrole-2-carboxylic acid, 4-(3,4-dimethoxyphenyl)-, ethyl ester
• CAS NO: 127572-59-2
• Molecular Formula: C15H17NO4
• Molecular Weight: 275.304
• Mol File: 127572-59-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-2-carboxylic acid, 4-(3,4-dimethoxyphenyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2-carboxylic acid, 4-(3,4-dimethoxyphenyl)-, ethyl ester(127572-59-2)
• EPA Substance Registry System: 1H-Pyrrole-2-carboxylic acid, 4-(3,4-dimethoxyphenyl)-, ethyl ester(127572-59-2)

Safety Data

• Hazardous Substances Data: 127572-59-2(Hazardous Substances Data)

Usage

Molecular Structure

The compound consists of a pyrrole ring with a carboxylic acid group (-COOH) attached to it, a 4-(3,4-dimethoxyphenyl) group, and an ethyl ester functional group (-OC2H5).

Chemical Class

It belongs to the class of pyrrole carboxylic acid derivatives, which are organic compounds known for their potential applications in medicinal chemistry.

Pharmacological Properties

The compound exhibits various pharmacological properties, making it a potential building block for the synthesis of pharmaceutical drugs and bioactive compounds.

Biological Activities

Its specific chemical properties and biological activities make it a subject of interest for researchers and scientists in the field of drug discovery and development.

Molecular Weight

285.32 g/mol

Physical State

The compound is likely a solid at room temperature, although the exact physical state is not specified in the provided material.

Solubility

The compound's solubility is not specified in the provided material, but it is likely soluble in organic solvents such as ethanol or methanol.

Reactivity

The compound may react with other chemicals, particularly those that can react with carboxylic acids or esters, but the specific reactivity is not specified in the provided material.

Upstream product

• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 516465-80-8 4-bromo-1H-pyrrole-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 623-33-6 glycine ethyl ester hydrochloride 
• 459-73-4 GlyOEt*HCl 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 433267-55-1 4-bromo-1H-pyrrole-2-carboxylic acid ethyl ester 
• 97176-88-0 2-(3,4-dimethoxyphenyl)trimethinium perchlorate 

Downstream Products

• 681431-22-1 5-bromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 181423-71-2 14-(3,4-dimethoxyphenyl)-2,3,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 681431-24-3 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 681431-23-2 4-(3,4-dimethoxyphenyl)-5-[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]-1H-pyrrole-2-carboxylic acid ethyl ester 
• 681431-25-4 2-bromo-1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 919082-30-7 ethyl 1,2-bis(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 681431-26-5 4-(3,4-dimethoxy-phenyl)-5-{4,5-dimethoxy-2-[2-(toluene-4-sulfonyloxy)-ethyl]-phenyl}-1H-pyrrole-2-carboxylic acid ethyl ester 
• 1346862-91-6 4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid n-hexyl ester 
• 1346862-96-1 4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid benzyl ester 
• 1346862-97-2 4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid N,N-dimethylaminopropyl ester 
• 1346862-99-4 4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid N,N-dimethylaminoethyl ester 
• 1346863-07-7 4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid 4-methoxyphenyl ester 
• 1346862-56-3 3,5-dibromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 1346862-57-4 3,5-dibromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid n-propyl ester 

Relevant articles and documents

One-pot synthesis of pyrroles using a titanium-catalyzed multicomponent coupling procedure

A simple one-pot procedure for the production of 2-carboxylpyrroles with 4-alkyl, 5-alkyl, 4-aryl, 4-aryl-5-alkyl, or 3,4-diaryl substitution patterns is presented. The procedure involves the titanium-catalyzed multicomponent coupling of alkynes, primary amines and isonitriles to give 1,3-diimines in situ; the multicomponent product is then treated with the ethyl ester of glycine hydrochloride to give the NH-pyrrole. The reaction can be carried out with the neutralized glycine ester or with the hydrochloride salt using DBU as a base. Yields of pyrrole based on starting alkyne varied from 25 to 65% over the one pot procedure, and in most cases only one regioisomer of the product is observed. Further, it is proposed that the regioselectivities of the reactions are a result of rate-determining ring closure after relatively fast transimination with glycine ethyl ester.

A Modular Synthesis of the Lamellarins: Total Synthesis of Lamellarin G Trimethyl Ether

A modular synthesis of the lamellarin family of natural products has been developed that is based on the application of three iterative halogenation/cross-coupling reaction sequences. The ability to halogenate the pyrrole core in a regioselective fashion, even in the presence of highly electron-rich aryl substituents, has been established. The compatibility of Suzuki coupling conditions with free alcohols and phenols in the boronic acids has been employed to reduce the number of protection/deprotection steps. Indeed, the presence of a free phenol on boronic acid 3 has been determined to be critical for the successful final coupling in route to lamellarin G trimethyl ether, since protected versions fail to undergo coupling.

Application of 2-Substituted Vinamidinium Salts to the Synthesis of 2,4-Disubstituted Pyrroles

A variety of 2-substituted vinamidinium salts react with α-amino acid esters under basic conditions to produce 2-carbethoxy-4-substituted-pyrroles in good yield.The overall process represents a short and efficient synthesis of highly functionalized pyrrol