38480-28-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromopyrrole is used as a reactant/reagent for the preparation and structure-activity relationship of trifluoroalkyl-containing azoles and arenes. These compounds serve as inhibitors of β-amyloid self-assembly, which is a crucial factor in the development of neurodegenerative diseases such as Alzheimer's. By inhibiting the self-assembly of β-amyloid, 2-bromopyrrole-based compounds can potentially help in the development of therapeutic agents for treating these diseases.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 2221, 1981 DOI: 10.1021/jo00324a005

Upstream product

• 109-97-7 pyrrole 

Downstream Products

• 1003-29-8 2-pyrrole aldehyde 
• 1245720-73-3 2-(2-nitrophenyl)-1H-pyrrole 
• 30068-53-2 2-bromo-1-phenyl-1H-pyrrole 
• 1963-43-5 (4-methoxyphenyl)(1H-pyrrol-2-yl)methanone 
• 63833-47-6 (4-nitrophenyl)(1H-pyrrole-2-yl)methanone 
• 13169-71-6 2-(4-chlorobenzoyl)pyrrole 
• 55895-62-0 2-(4-methylbenzoyl)pyrrole 
• 2557-70-2 2-(trifluoroacetyl)pyrrole 
• 290306-56-8 2-bromo-1-(p-toluenesulfonyl)pyrrole 
• 117657-37-1 2-bromo-pyrrole-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Preparation method of vonoprazan intermediate

The invention provides a preparation method of a vonoprazan intermediate. Specifically, the vonoprazan intermediate is obtained through a bromination reaction, a sulfonylation reaction, a Vilsmeier reaction and a Suzuki reaction. According to the preparation method, dangerous hydrogenation reaction and low-temperature reaction are avoided, and the reaction has the advantages of mild conditions, easiness in operation, cheap raw materials, low production cost and high total yield.

A halogenated nitrogen-containing unsaturated cyclic hydrocarbon preparation method

The invention discloses a halogenated nitrogen-containing unsaturated cyclic hydrocarbon of the preparation method, the steps of: (1) the nitrogen-containing unsaturated cyclic hydrocarbon dissolved in hydrochloric acid or hydrobromic acid, addition of an oxidizing agent, the reaction system halogenated reaction, in the reaction process timing sampling detection, when detecting the target product quality of a halide accounted for is a reaction system in the total of the organic matter of 70% - 95% when, added to the reaction system in the terminator to terminate reaction, to obtain containing nitrogen-containing unsaturated cyclic hydrocarbon feed; (2) to the liquid mixed into the organic solvent extraction, extraction to obtain the organic phase, the organic phase temperature is reduced to make the solid precipitation or distilling the organic solvent to obtain a liquid product to be deducted, the resulting solid or liquid product is halogenated nitrogen-containing unsaturated cyclic hydrocarbon. The method solves the problem of the nitrogen-containing unsaturated cyclic hydrocarbon over [...] reaction problems.

Original design of fluorescent ligands by fusing BODIPY and melatonin neurohormone

An original design and synthesis of fluorescent ligands for melatonin receptor studies is presented and consists in the fusion of the endogenous ligand with the fluorescent BODIPY core. Probes I-IV show high affinities for MT1 and MT2 melatonin receptors and exhibit fluorescence properties compatible with cell observation.

S2 emission from chemically modified BODIPYs

Novel boron dipyrromethene (BODIPY) derivatives having significant absorption and emission in the longer wavelength region were synthesized. BODIPY showed anomalous S2 emission from the second excited (S2) state at shorter wavelength

A versatile, modular synthesis of monofunctionalized BODIPY dyes

A careful choice of the pyrrole building blocks allows the synthesis of a wide range of monohalogenated BODIPY dyes with excellent reactivity in palladium catalyzed coupling reactions. The Royal Society of Chemistry 2009.

LEWIS ACID CATALYZED HALOGENATION OF ACTIVATED CARBON ATOMS

A practical and efficient method for halogenation of activated carbon atoms using readily available /V-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.

Lewis acid catalyzed highly selective halogenation of aromatic compounds

A simple and efficient procedure for the halogenation of aromatic compounds with NCS, NBS, NIS and NFSI in the presence of catalytic amount of ZrCl 4 is described. Chlorination, bromination, iodination and fluorination of various aromatic compounds are performed with high selectivity under mild reaction conditions. Georg Thieme Verlag Stuttgart.

2-Bromo-N-(p-toluenesulfonyl)pyrrole: A Robust Derivative of 2-Bromopyrrole

2-Bromo-AL(p-toluenesulfonyl)pyrrole (2), a crystalline stable derivative of 2-bromopyrrole (1) has been prepared in 80% yield by bromination of pyrrole, followed by conversion to the N-(p-toluenesulfonyl) derivative. This compound is stable indefinitely at ambient temperature. Compound 2 is an excellent substrate for Suzuki coupling with arylboronic acids.

Antibacterial agents

PCT No. PCT/US97/22356 Sec. 371 Date Mar. 29, 1999 Sec. 102(e) Date Mar. 29, 1999 PCT Filed Dec. 5, 1997 PCT Pub. No. WO98/25932 PCT Pub. Date Jun. 18, 1998Described are antibacterial agents of formula (I): X is O, S or N-R8; R1, R2, R3 and R8 are independently H, straight or branched alkyl of 1-6 carbons, cycloalkyl of 3-6 carbons, alkenyl or alkynyl of from 2 to 6 atoms, R heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur, or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR2, NR'COR', CN, CO2R' or CONR2', halogen, CN, CO2R, COR, CON(R)2, CON(R'')2, SR, SON, SCO2R or SCON(R)2; R4 is H, straight or branched alkyl of from 1-6 carbon atoms, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR2, NR'COR', CN, CO2R' or CONR2', halogen, CN, NO2, N(R)2, NRCOR, NRCOR'', COR, CO2R, CON(R)2, CON(R'')2, NRCON(R)2, NRCO2R; R5 is 1-6 straight or branched alkyl, a cycloalkyl of 3-6 carbons, alkenyl or alkynyl of from 2 to 6 atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur or phenyl, all of which rings may be optionally substituted up to 3 times by halogen, OR, NR2, NR'COR', CN, CO2R' or CONR2', halogen, OR, N(R)2, NRCOR, NRCOR'', COR, CON(R)2, CON(R'')2, SR or SO2R; R6, R7 are independently H, straight or branched alkyl of 1-6 carbons, cycloalkyl of 3-6 carbons, COR, COR'', SO2NR2, CONR2 and these may be optionally substituted by any of the groups listed for R5; R is H, straight or branched alkyl of 1-6 carbon atoms, cycloalkyl of from 3-6 carbon atoms, heterocyclic ring of from 5-8 atoms with 1-3 heteroatoms as nitrogen, oxygen or sulfur, or pheny, all of which may be optionally substituted by halogen, OR', NR'2, NR'COR', CN, CO2R', CONR'2, R' is H, alkyl of from 1-3 carbon atoms or Ph; R'' is part of a naturally occurring amino acid connected via an amide or acyl bond as determined by the formula; halogen is any one of fluoro, chloro, bromo or iodo; or a pharmaceutically acceptable salt.

Condensation reactions of a nitrodienamine with organocopper and alkyllithium reagents prepared from pyrrole derivatives

Condensation reactions of a nitrodienamine (1) with Grignard, organocopper and alkyllithium reagents prepared from pyrrole derivatives were investigated.