94446-97-6

Usage

Uses

Used in Organic Synthesis:
2-Bromo-3-(bromomethyl)pyridine is used as a building block for the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Bromo-3-(bromomethyl)pyridine is used as a reagent in the development of new drugs. Its versatile chemical properties allow it to be incorporated into drug molecules, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Development:
2-Bromo-3-(bromomethyl)pyridine is also utilized in the development of agrochemicals, such as pesticides and herbicides. Its ability to form stable compounds with other molecules makes it a useful component in the creation of effective agricultural chemicals.
Used in Manufacturing Pharmaceutical Intermediates:
This chemical compound is used in the production of pharmaceutical intermediates, which are essential precursors in the synthesis of final drug products. Its presence in intermediates can contribute to the overall effectiveness and safety of the final drug.
Used in Research Chemicals:
2-Bromo-3-(bromomethyl)pyridine is employed as a research chemical, providing scientists with a valuable tool for studying various chemical reactions and processes. Its unique properties can help researchers gain insights into the behavior of brominated pyridine derivatives and their potential applications in various fields.

InChI:InChI=1/C6H5Br2N/c7-4-5-2-1-3-9-6(5)8/h1-3H,4H2

Upstream product

• 3430-17-9 2-bromo-3-picoline 
• 131747-54-1 (2-bromopyrid-3-yl)methanol 
• 109-04-6 2-bromo-pyridine 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 35905-85-2 2-bromonicotinic acid 

Downstream Products

• 159898-42-7 5-(Benzyl-methyl-amino)-3-(2-bromo-pyridin-3-ylmethyl)-3-(3,4-dimethoxy-phenyl)-pentan-2-one 
• 131747-54-1 (2-bromopyrid-3-yl)methanol 
• 380614-80-2 3-[2-(2-bromo-pyridin-3-yl)-ethyl]-pyridine-2-carboxylic acid phenylamide 
• 491879-09-5 2-(2-bromopyridin-3-ylmethyl)cyclohexanone 
• 496790-55-7 (R)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester 
• 496790-54-6 (S)-2-(benzhydrylidene-amino)-3-(2-bromopyridin-3-yl)-propionic acid tert-butyl ester 
• 874947-65-6 2-(2-bromopyridin-3-ylmethyl)-2-methylcyclohexanone 
• 874947-66-7 3-(2-bromopyridin-3-ylmethyl)-2-methyl-4-oxocyclohex-2-enecarboxylic acid methyl ester 
• 496790-56-8 (S)-tert-butyl 1-benzhydryl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate 
• 264625-65-2 3-(azidomethyl)-2-phenylpyridine 
• 264625-60-7 (2-bromo-3-pyridinyl)methyl diphenylphosphinate 
• 936107-36-7 2-bromo-3-(1-piperidinylmethyl)pyridine 
• 1185105-99-0 (-)-2-bromo-3-({[(1S)-1-methyl-3-(4-methylphenyl)prop-2-yn-1-yl]oxy}methyl)pyridine 
• 1207736-72-8 C₅H₃NBrCH₂SC₆H₅ 

Relevant academic research and scientific papers

tBuOK-Promoted Cyclization of Imines with Aryl Halides

A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

Cross-coupling strategy for the synthesis of diazocines

Ethylene bridged azobenzenes are novel, promising molecular switches that are thermodynamically more stable in the (Z) than in the (E) configuration, contrary to the linear azobenzene. However, their previous synthetic routes were often not general, and yields were poorly reproducible, and sometimes very low. Here we present a new synthetic strategy that is both versatile and reliable. Starting from widely available 2-bromobenzyl bromides, the designated molecules can be obtained in three simple steps.

S29434, a quinone reductase 2 inhibitor: Main biochemical and cellular characterization

Quinone reductase 2 (QR2, E.C. 1.10.5.1) is an enzyme with a feature that has attracted attention for several decades: in standard conditions, instead of recognizing NAD(P)H as an electron donor, it recognizes putative metabolites of NADH, such as N-methyl- and N-ribosyl-dihydronicotinamide. QR2 has been particularly associated with reactive oxygen species and memory, strongly suggesting a link among QR2 (as a possible key element in pro-oxidation), autophagy, and neurodegeneration. In molecular and cellular pharmacology, understanding physiopathological associations can be difficult because of a lack of specific and powerful tools. Here, we present a thorough description of the potent, nanomolar inhibitor [2-(2-methoxy-5H-1,4b,9-triaza(indeno[2,1-a]inden-10-yl)ethyl]-2-furamide (S29434 or NMDPEF; IC505 5–16 nM) of QR2 at different organizational levels. We provide full detailed syntheses, describe its cocrystallization with and behavior at QR2 on a millisecond timeline, show that it penetrates cell membranes and inhibits QR2-mediated reactive oxygen species (ROS) production within the 100 nM range, and describe its actions in several in vivo models and lack of actions in various ROS-producing systems. The inhibitor is fairly stable in vivo, penetrates cells, specifically inhibits QR2, and shows activities that suggest a key role for this enzyme in different pathologic conditions, including neurodegenerative diseases.

Preparation of 1,5-Dihydropyrazolo[3′,4′:5,6]pyrano[3,4- b]pyridines via a Microwave-Assisted, Palladium-Catalyzed Regioselective C-H Heteroarylation of Electron-Rich Pyrazoles

Here we report the first synthesis of a family of novel heterocyclic compounds based on a 5-dihydropyrazolo[3′,4′:5,6]pyrano[3,4-b]pyridine core. In the course of our drug discovery programs, we had need to access the previously unknown 5-dihydropyrazolo[3′,4′:5,6]pyrano[3,4-b]pyridine core. Initial attempts required long reaction times, which led to degradation and side products. Reaction optimization identified a Pd-catalyzed, microwave-assisted C-H heteroarylation protocol for the rapid, general, and high yielding synthesis of this tricyclic core (as well as related analogs) suitable to drive optimization efforts.

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

AZAINDOLINE COMPOUNDS AS GRANZYME B INHIBITORS

Azaindoline compounds as granzyme B inhibitors, compositions that include the compounds, and methods for using the compounds. Methods for treating cutaneous scleroderma, epidermolysis bullosa, radiation dermatitis, alopecia areata, and discoid lupus erythematosus are provided.

Covalent granzyme B inhibitors

Covalent Granzyme B inhibitors, compositions that include the compounds, and methods for using the compounds. A method for treating cutaneous scleroderma, epidermolysis bullosa, radiation dermatitis, alopecia areata, and discoid lupus erythematosus are pr

Substituted quinazolinones as kinase inhibitors endowed with anti-fibrotic properties

Some new 3-substituted quinazolinones were synthesized and evaluated as inhibitors of kinases involved in fibrogenic process. The compounds were tested against a panel of both tyrosine and serine-threonine kinases. The profile of selectivity of some representative compounds was investigated through molecular docking studies. The most interesting compounds were also evaluated in vitro as potential agents for the treatment of fibrotic diseases. Quinazolinone derivatives reduced proliferation and expression of genes involved in the fibrogenic process in hepatic stellate cells (HSCs) and intestinal subepithelial myofibroblasts (ISEMFs). Furthermore some compounds downregulated phosphorylation of p38MAPK. Our findings provide evidences that 3-substituted quinazolinones target multiple essential pathways of the fibrogenic process.

CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines

A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.

SELECTIVE CYP11B1 INHIBITORS FOR THE TREATMENT OF CORTISOL DEPENDENT DISEASES

The present invention relates to compounds which selectively inhibit CYP11B1. Preferably, the compounds of the present invention do not substantially inhibit CYP11B2. Moreover, the compounds of the present invention do not substantially inhibit CYP17 and/or CYP19, either. Amongst other applications of the compounds of the present invention, they can be used for the treatment of Cushing's syndrome or metabolic disease.