931-03-3

Usage

Uses

Used in Pharmaceutical Industry:
Pyrrole-3-carboxylic acid is used as a key intermediate in the synthesis of isoindolinone compounds, which serve as cereblon inhibitors and GSPT1 degraders. These compounds have potential applications in the development of novel therapeutic agents for the treatment of various diseases, including cancer and other disorders.
In the preparation of isoindolinone compounds, pyrrole-3-carboxylic acid plays a crucial role in the formation of the core structure, which is responsible for the biological activity of the final product. The versatility of pyrrole-3-carboxylic acid allows for the design and synthesis of a wide range of isoindolinone derivatives with diverse pharmacological properties, making it a valuable building block in medicinal chemistry.
Furthermore, the unique chemical properties of pyrrole-3-carboxylic acid, such as its ability to form stable complexes with metal ions and its potential to act as a chelating agent, may also contribute to its utility in various other applications, including the development of new materials and catalysts. However, more research is needed to fully explore and understand the potential uses of pyrrole-3-carboxylic acid beyond its current applications in the pharmaceutical industry.

Upstream product

• 85684-93-1 1-tritylpyrrole-3-carboxylic acid 
• 109-97-7 pyrrole 
• 124-38-9 carbon dioxide 

Downstream Products

• 2703-17-5 methyl 1H-pyrrole-3-carboxylate 
• 134226-26-9 N-(m-vinylphenyl)-1-H-pyrrole-3-carboxamide 
• 134226-24-7 N-(p-vinylphenyl)-1-H-pyrrole-3-carboxamide 
• 134226-18-9 p-vinylbenzyl 1-H-pyrrole-3-carboxylate 
• 37964-17-3 pyrrole-3-carboxylic acid ethyl ester 
• 195325-39-4 (C₅H₅)Fe(CO)2(SCOC₆H₄CO₂COC₄H₄N) 
• 1030613-43-4 4-(2-bromo-5-fluorophenoxy)-1-[5-(1H-pyrrol-3-yl)-[1,2,4]-oxadiazol-3-yl]piperidine 
• 71803-59-3 3-hydroxymethyl-1H-pyrrole 
• 7126-39-8 pyrrole-3-carboxaldehyde 
• 881676-32-0 5-bromo-1H-pyrrole-3-carboxaldehyde 

Relevant academic research and scientific papers

Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

The Lewis acid-mediated carboxylation of arenes with CO2 has been successfully applied to 1-substituted indoles and pyrroles by using dialkylaluminum chlorides instead of aluminum trihalides. Thus, the carboxylation of 1-methylindoles, 1-benzyl-, and 1-phenylpyrroles proceeds regioselectively with the aid of an equimolar amount of Me2AlCl under CO2 pressure (3.0 MPa) at room temperature to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in 61-85% yields, while the same treatment of 1,2,5-trimethylpyrrole affords the 3-carboxylic acid in 52% yield.

The Protecting-Directing Role of the Trityl Group in Syntheses of Pyrrole Derivatives: Efficient Preparations of 1-H-Pyrrole-3-carboxylic Acid and 3-Acyl, 3-Amino, and 3-Bromo-1-tritylpyrroles

Trifluoroacetylation, formylation, and bromination of 1-tritylpyrrile occur regioselectively at the 3-position in high yields.Quantitative hydrolysis of the 3-trifluoroacetyl derivative and removal of the trityl group from the resulting acid with sodium in liquid ammonia furnishes a new, short, high-yielding synthessis of the simple 1-H-pyrrole-3-carboxylic acid. 1-Tritylpyrrole-3-carboxylic acid has been converted efficiently into 3-aminopyrroles via Curtius rearrangement of the derived azide: 3-amino-1-tritylpyrrole appears to exist in solution exclusively as its imino-Δ4-pyrroline tautomer. 1-H-3-t-Butyloxycarbonylaminopyrrole udergoes trifluoroacetylation regioselectively at the 2-position.Metallation of 1-tritylpyrrole with butyl-lithium in hexamethylphosphoric triamide gives rise to the unexpected products 9-phenylfluorene, 1-methoxycarbonylpyrrole and methyl triphenylmethylacetate (after work-up of the lithio-intermediates with carbon dioxide and methylation of the resulting acids).