52459-90-2

Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, methyl ester (9CI) is used as a key intermediate in the synthesis of various drugs and pharmaceutical compounds for its versatile chemical properties and potential pharmacological activities.
Used in Organic Synthesis:
1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, methyl ester (9CI) is used as a building block in the creation of complex molecules, contributing to the development of new chemical entities with potential applications in various fields.

InChI:InChI=1/C8H11NO2/c1-5-4-9-6(2)7(5)8(10)11-3/h4,9H,1-3H3

Upstream product

• 90433-95-7 methyl 5-(2-methyl-1,3-dithiolan-2-yl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylate 
• 73857-68-8 2-methyl-1,3-dithiolan-2-yl perchlorate 
• 107-41-5 2-methyl-2,4-pentanediol 
• 62264-99-7 methyl 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate 
• 107-21-1 ethylene glycol 
• 540-63-6 ethane-1,2-dithiol 
• 112561-10-1 methyl-bis(trimethylsilyl)aminomethylpropiolate 
• 75-36-5 acetyl chloride 
• 18913-35-4 methyl buta-2,3-dienoate 
• 90433-94-6 methyl 2,4-dimethyl-5-(2-methyl-1,3-dithiolan-2-yl)-1H-pyrrole-3-carboxylate 
• 1286715-92-1 C₈H₁₃NO₃ 

Downstream Products

• 154700-02-4 benzyl 3-ethyl-4'-methoxycarbonyl-4,3',5'-trimethyl-2,2'-dipyrrylmethane-5-carboxylate 
• 138648-25-6 benzyl 3-ethyl-4'-methoxycarbonyl-3',5'-dimethyl-2,2'-dipyrrylmethane-5-carboxylate 
• 138648-41-6 benzyl 3,8,17-triethyl-2,12,18-trimethyl-13,15-(13'-oxo)ethanoporphyrin-15'-carboxylate 
• 138648-40-5 3-Oxo-3-((1Z,4Z,9Z,15Z)-7,12,18-triethyl-3,13,17-trimethyl-porphyrin-2-yl)-propionic acid benzyl ester 

Relevant academic research and scientific papers

Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes

The regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium-catalyzed isomerization of easily prepared O-allyl oximes enables rapid access to O-vinyl oximes. The regioselectivity of pyrrole formation can be controlled by either the identity of the α-substituent or through the addition of an amine base. When enolization is favored, a [3,3] rearrangement followed by a Paal-Knorr cyclization provides a 2,3,4-trisubstituted pyrrole; when enolization is disfavored, a [1,3] rearrangement occurs prior to enolization to produce a 2,3,5-trisubstituted pyrrole after cyclization. Optimization and scope of the O-allyl oxime isomerization and subsequent pyrrole formation are discussed and mechanistic pathways are proposed. Conditions are provided for selecting either the [3,3] rearrangement or the [1,3] rearrangement product with β-ester O-allyl oxime substrates.

Palladium catalysed synthesis of pyrroles from enamines

Substituted pyrroles are formed in moderate to good yields by the Pd- catalysed cyclisation of enamines containing β-vinyl bromide functionalities.

Aminosilanes in Organic Synthesis. Addition of Organocopper Reagents on γ-Bis(trimethylsilyl)amino-α-Acetylenic Amides, Esters and Ketones. Stereochemistry und Some Synthetic Uses

The stereochemical outcome of the carbocupration of γ-bis(trimethylsilyl)amino-α-acetylenic amide, esters and ketone was studied.A judicious choice of substrate, reagent and(or) reaction conditions allows to perform highly stereoselective cis or trans addition.The intermediate vinylic copper adducts, with (E) or (Z) configuration, react with electrophilic reagents to provide short routes to substituted pyrrolinones and pyrroles.Keywords: Silylamines, propargylamines, organocopper regaents, stereochemistry, nitrogen heterocycles.

Preparation of 2-Methoxy-Substituted Pyrroles by Aza-Wittig Reactions

α-Halo ketones and dimethyl malonate can be transformed by Knoevenagel condensation and nucleophile displacement of halogen with sodium azide into the azide esters 10.These azides undergo ring closure to 2-methoxy-substituted pyrroles 11 by intramolecular

SILYLAMINES IN ORGANIC SYNTHESIS : A NEW ACCESS TO FUNCTIONAL PYRROLES VIA ORGANOCUPRATES ADDITION ON METHYL-BIS(TRIMETHYLSILYL)AMINOMETHYLPROPIOLATE

Organocuprate addition reactions on methyl-bis(trimethylsilyl)aminomethylpropiolate lead to the formation of a Z-vinyl cuprate with a high stereoselectivity.Upon reaction of acid chloride, pyrroles are formed by a spontaneous intramolecular cyclisation of the intermediate Z-silylamino enone.Various functional substituted pyrroles can be obtained in one step by this route.

Deacylation of Pyrrole and other Aromatic Ketones

Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate (1a) reacts rapidly with ethylene glycol in refluxing benzene with p-toluenesulfonic acid or perchloric acid as a catalyst to give ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3) in high yield (96 percent).Various 2- and 3-acylpyrroles can be efficiently deacylated by using this procedure.Other ketones which undergo deacylation include phenyl(2-phenylindol-3-yl)methanone (19), 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone (20), and 2,4-dimethoxybenzophenone.Certain pyrrole ketones where the acyl group is flanked by two ring methyl groups are also cleaved under acidic conditions by using ethanedithiol.