934-07-6

Basic information

• Product Name: methyl 5-bromo-1H-pyrrole-2-carboxylate
• Synonyms: 5-bromo-1H-Pyrrole-2-carboxylic acid methyl ester;1H-Pyrrole-2-carboxylic acid, 5-bromo-, methyl ester
• CAS NO: 934-07-6
• Molecular Formula: C₆H₆BrNO₂
• Molecular Weight: 204.022
• Mol File: 934-07-6.mol

Chemical Properties

• Melting Point: 101-103 °C
• Boiling Point: 290.485°C at 760 mmHg
• Flash Point: 129.481°C
• Appearance: /
• Density: 1.675g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.18±0.50(Predicted)
• CAS DataBase Reference: methyl 5-bromo-1H-pyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-bromo-1H-pyrrole-2-carboxylate(934-07-6)
• EPA Substance Registry System: methyl 5-bromo-1H-pyrrole-2-carboxylate(934-07-6)

Safety Data

• Hazardous Substances Data: 934-07-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 5-bromo-1H-pyrrole-2-carboxylate is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity allow for the development of novel drugs with potential therapeutic applications. The bromine atom at the 5-position of the pyrrole ring can be replaced or modified through various chemical reactions, enabling the creation of a wide range of pharmaceutical agents.
In the pharmaceutical industry, methyl 5-bromo-1H-pyrrole-2-carboxylate serves as a building block for the development of new drugs, particularly those targeting specific biological pathways or receptors. Its versatility in chemical reactions allows for the fine-tuning of drug properties, such as solubility, stability, and bioavailability, which are crucial for the effectiveness and safety of pharmaceutical products.
Furthermore, the use of methyl 5-bromo-1H-pyrrole-2-carboxylate in pharmaceutical synthesis can lead to the discovery of innovative treatments for various diseases and conditions, contributing to the advancement of medical science and improving the quality of life for patients worldwide.

InChI:InChI=1/C6H6BrNO2/c1-10-6(9)4-2-3-5(7)8-4/h2-3,8H,1H3

Upstream product

• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 117067-98-8 α-(dimethylamino)-α-(pyrrol-2-yl)acetonitrile 

Downstream Products

• 943587-56-2 (S)-6-bromo-2-(2,4-dimethoxy-benzyl)-4-vinyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one 
• 1323077-16-2 5-bromo-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylic acid methyl ester 
• 1323075-26-8 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-8-carbonitrile 
• 1323075-28-0 10a-(4-methoxyphenyl)-8-methyl-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one 
• 1323075-30-4 8-ethynyl-10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one 
• 1323077-19-5 8-bromo-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one 
• 1323077-20-8 10a-(4-methoxyphenyl)-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-8-carbonitrile 
• 1323077-22-0 10a-(4-methoxyphenyl)-8-methyl-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one 
• 1323077-24-2 10a-(4-methoxyphenyl)-8-[(trimethylsilyl)ethynyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one 
• 1323077-26-4 8-ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one 
• 1518920-27-8 6-bromo-3-(4-trifluoromethylphenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one 
• 1518920-41-6 1-oxo-3-(4-trifluoromethylphenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbaldehyde 
• 1518920-10-9 1-oxo-3-(4-trifluoromethylphenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile 
• 1518920-12-1 N-hydroxy-1-oxo-3-(4-trifluoromethylphenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carboxamidine 

Relevant articles and documents

Substrate Controlled Regioselective Bromination of Acylated Pyrroles Using Tetrabutylammonium Tribromide (TBABr3)

Electrophilic bromination of pyrroles bearing carbonyl substituents at C-2 typically results in a mixture of the 4- and 5-brominated species, generally favoring the 4-position. Herein, we describe a substrate-controlled regioselective bromination in which

3-(PYRIDIN-3-YL)-ACRYLAMIDE AND N-(PYRIDIN-3-YL)-ACRYLAMIDE DERIVATIVES AND THEIR USE AS PAK OR NAMPT MODULATORS

The invention generally relates to cyclic compounds and, more particularly, to a compound represented by Structural Formula I: or a pharmaceutically acceptable salt thereof and pharmaceutical compositions comprising the multicyclic compounds. The invention also relates to a method for treating a disease or disorder selected from cancer (e.g., lymphoma, such as mantle cell lymphoma), a neurodegenerative disease, an inflammatory diseases or an immune system disease (e.g., a T- Cell mediated autoimmune diseases) in a subject in need thereof. The method comprises administering to a subject in need thereof a therapeutically effective amount of a compound of the invention, or a pharmaceutically acceptable salt thereof, or a composition comprising a compound of the invention, or a pharmaceutically acceptable salt thereof.

Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles

Bromoperoxidases from the brown alga Ascophyllum nodosum, abbreviated as VBrPO(AnI) and VBrPO(AnII), show 41% sequence homology and differ by a factor of two in the percentage of α-helical secondary structures. Protein monomers organize into homodimers for VBrPO(AnI) and hexamers for VBrPO(AnII). Bromoperoxidase II binds hydrogen peroxide and bromide by approximately one order of magnitude stronger than VBrPO(AnI). In oxidation catalysis, bromoperoxidases I and II turn over hydrogen peroxide and bromide similarly fast, yielding in morpholine-4-ethanesulfonic acid (MES)-buffered aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon-bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with larger energy gaps between the π-type HOMO of, for example, an alkene and the σ*Br,X-type LUMO of the bromination reagent. By using this approach, the reactivity of substrates and selectivity for carbon-bromine bond formation in reactions mediated by vanadate-dependent bromoperoxidases become predictable, as exemplified by the synthesis of bromopyrroles occurring naturally in marine sponges of the genera Agelas, Acanthella, and Axinella. The Royal Society of Chemistry.

A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a domino coupling-isomerization-condensation reaction

A novel Pd/Cu catalyzed domino reaction for the synthesis of functionalized pyrrolo[1,2-b]pyridazines from readily accessible (hetero)aryl propargyl alcohols and 1-amino-2-bromopyrroles was developed. This cascade process involves a Sonogashira cross-coupling reaction, an isomerization and an intramolecular condensation.

Molecular cloning, structure, and reactivity of the second bromoperoxidase from Ascophyllum nodosum

The sequence of bromoperoxidase II from the brown alga Ascophyllum nodosum was determined from a full length cloned cDNA, obtained from a tandem mass spectrometry RT-PCR-approach. The clone encodes a protein composed of 641 amino-acids, which provides a mature 67.4 kDa-bromoperoxidase II-protein (620 amino-acids). Based on 43% sequence homology with the previously characterized bromoperoxidase I from A. nodosum, a tertiary structure was modeled for the bromoperoxidase II. The structural model was refined on the basis of results from gel filtration and vanadate-binding studies, showing that the bromoperoxidase II is a hexameric metalloprotein, which binds 0.5 equivalents of vanadate as cofactor per 67.4 kDa-subunit, for catalyzing oxidation of bromide by hydrogen peroxide in a bi-bi-ping-pong mechanism (kcat = 153 s-1, 22 °C, pH 5.9). Bromide thereby is converted into a bromoelectrophile of reactivity similar to molecular bromine, based on competition kinetic data on phenol bromination and correlation analysis. Reactivity provided by the bromoperoxidase II mimics biosynthesis of methyl 4-bromopyrrole-2-carboxylate, a natural product isolated from the marine sponge Axinella tenuidigitata.

Vanadate(v)-dependent bromoperoxidase immobilized on magnetic beads as reusable catalyst for oxidative bromination

Vanadate(v)-dependent bromoperoxidase I (Ascophyllum nodosum) was immobilized on magnetic micrometre-sized particles in quantitative yields, with up to 40% retention of initial bromoperoxidase (BPO) activity. The immobilized enzyme was stable with a half-life time of about 160 days. It served as reusable catalyst for bromide oxidation with H2O2 in up to 14 consecutive experiments. Reactivity that resulted from enzymatic bromide oxidation was applicable for methyl pyrrole-2-carboxylate conversion into derivatives of naturally occurring compounds (e.g. from Agelas oroides) with product selectivity of up to 75%.

Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations

Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 °C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 μmol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4- ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2- carboxamide (from Acanthella carteri).

A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: agelastatin

In this article, we report a full account of our recent development of pyrroles and N-alkoxyamides as new classes of nucleophiles for palladiumcatalyzed AAA reactions, along with application of these methodologies in the total synthesis of agelastatin A,

New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A

New classes of nucleophiles, pyrroles, and N-methoxyamides were developed for Pd-catalyzed AAA reactions. By varying the functional groups at the 2-position of pyrroles, either regioisomer of the piperazinone is available. Using one regioisomer, the total

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Compounds of the formula: where the formula variables are as defined in the disclosure, advantageously inhibit or block the biological activity of the picomaviral 3C protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with one or more picomaviruses, such as RVP. Intermediates and synthetic methods for preparing such compounds are also described.