24255-97-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-BROMO-6-PIPERIDINOPYRIDINE is used as a building block for the synthesis of various pharmaceuticals and agrochemicals due to its versatile reactivity and ability to undergo multiple chemical transformations. This makes it a key intermediate in the creation of new compounds with potential therapeutic and pesticidal properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-BROMO-6-PIPERIDINOPYRIDINE is utilized as a starting material for the development of new drugs. Its potential applications include being studied for its antifungal and antiviral properties, which could lead to the discovery of novel treatments for various infections and diseases.
Used in Organic Synthesis:
2-BROMO-6-PIPERIDINOPYRIDINE is employed as an important chemical in organic synthesis, where its unique structure and reactivity allow for the creation of a wide range of organic compounds. This versatility makes it a valuable tool for chemists in designing and synthesizing new molecules with specific functions and properties.

InChI:InChI=1/C10H13BrN2/c11-9-5-4-6-10(12-9)13-7-2-1-3-8-13/h4-6H,1-3,7-8H2

Upstream product

• 110-89-4 piperidine 
• 626-05-1 2,6-Dibromopyridine 

Downstream Products

• 3980-49-2 2,6-di(piperidine-1-yl)pyridine 
• 1360567-62-9 C₁₇H₂₀N₂O 
• 1360567-57-2 2-phenyl-6-(piperidin-1-yl)pyridine 
• 1309609-85-5 2-(2-(diethoxymethyl)phenyl)-6-(piperidin-1-yl)pyridine 
• 1220595-97-0 benzyl 2-(6-(piperidin-1-yl)pyridin-2-yl)ethylcarbamate 
• 1114064-25-3 6-(3-chlorophenyl)-6-methyl-3-(6-(piperidin-1-yl)pyridin-2-yl)-1,3-oxazinan-2-one 
• 1130556-38-5 N-methyl-N-phenyl-6-piperidin-1-ylpyridin-2-amine 

Relevant academic research and scientific papers

SUBSTITUTED TETRAHYDROPYRIDINE DERIVATIVES AS IDO-1 INHIBITORS AND USES THEREOF

Compounds of formula I that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase, pharmaceutical compositions including such compounds and methods of treating diseases, conditions or disorders utilizing such compounds and compositions.

ALLOSTERIC MODULATORS OF THE CANNIBINOID 1 RECEPTOR

The present technology relates to compounds and compositions of Formulas I, II, VII, and VIII, and methods using such compounds. The compounds and compositions described herein may be used in the treatment or prophylaxis of addiction, metabolic syndrome, obesity, and/or a CB1 receptor-medited disorder.

Diarylureas as allosteric modulators of the cannabinoid CB1 receptor: Structure-activity relationship studies on 1-(4-chlorophenyl)-3-{3-[6-(pyrrolidin-1-yl)pyridin-2-yl]phenyl}urea (PSNCBAM-1)

The recent discovery of allosteric modulators of the CB1 receptor including PSNCBAM-1 (4) has generated significant interest in CB1 receptor allosteric modulation. Here in the first SAR study on 4, we have designed and synthesized a series of analogs focusing on modifications at two positions. Pharmacological evaluation in calcium mobilization and binding assays revealed the importance of alkyl substitution at the 2-aminopyridine moiety and electron deficient aromatic groups at the 4-chlorophenyl position for activity at the CB1 receptor, resulting in several analogs with comparable potency to 4. These compounds increased the specific binding of [3H]CP55,940, in agreement with previous reports. Importantly, 4 and two analogs dose-dependently reduced the Emaxof the agonist curve in the CB1 calcium mobilization assays, confirming their negative allosteric modulator characteristics. Given the side effects associated with CB1 receptor orthosteric antagonists, negative allosteric modulators provide an alternative approach to modulate the pharmacologically important CB1 receptor.

Access to 2-Aminopyridines - Compounds of great biological and chemical significance

2-Aminopyridines are key structural cores of bioactive natural products, medicinally important compounds, and organic materials and thus, extremely valuable synthetic targets. The few reported 6-substituted 2-aminopyridines and the lack of flexible, efficient and general applicable methods for their synthesis demonstrates the urgent need of new methods for their preparation. Reactions between 2,6-dibromopyridine and primary or secondary, cyclic or acyclic, and aliphatic or aromatic amines were shown to selectively yield the respective 6-bromopyridine-2-amines in very high yields which were successfully used as substrates for subsequent C-C cross-coupling reactions. The recently introduced dichloro-bis[1-(dicyclohexylphosphanyl)piperidine]palladium (1) was used as catalyst for the cross-coupling of 6-bromopyridine-2-amines with arylboronic acids, diaryl- and dialkylzinc reagents or olefins and hence, is also an excellent C-C cross-coupling catalyst for this type of substrate. Moreover, all the reaction protocols presented were in each of the catalyses uniformly applied. The scope of both the amination and the cross-coupling reactions are well defined and allow one to simply adapt the reaction protocols directly to other amines and/or coupling partners and, thus, provide for the first time a very flexible and generally applicable reaction protocol to get access to 2-aminopyridines.

Transition metal-free amination of aryl halides-A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines

A simple and reliable reaction protocol for the clean, fast, and high-yielding synthesis of various N-arylated amines derived from reactions of aryl halides with various (also sterically hindered) amines under transition metal-free reaction conditions is presented. Dioxane and KN(Si(CH3)3)2 were found to be the ideal solvent and base for this transformation. The conversion rates and yields observed are excellent and in the majority of the reactions performed significantly higher than that obtained in their catalyzed versions. Furthermore, the selective synthesis of 6-halopyridin-2-amines and asymmetric pyridine-2,6-diamines (derived from consecutive reactions of 2,6-dibromopyridine and 2,6-dichloropyridine, respectively, with different amines) is possible in almost quantitative yields (relative to 2,6-dihalopyridine) within very short reaction times. Purification of the 6-halopyridin-2-amine intermediates is not necessary, allowing the synthesis of pyridine-2,6-diamines in 'one-pot'. However, catalysts are in many cases not required to efficiently and selectively couple aryl halides with amines, making transition metal-free versions of the Buchwald-Hartwig reaction extremely attractive for the synthesis of N-arylated amines with substrates containing substituents on the aryl halide, which either promote regioselectivity and/or do not require regioselective aminations.

Role of copper in catalyzing aryl and heteroaryl-nitrogen (or -oxygen) bond formation under ligand-free and solvent-free conditions

Formation of aryl- or heteroaryl-nitrogen (or -oxygen) bonds under ligand and solvent-free conditions are highly selective to the presence of copper. While bromoarenes undergo C-N (or -O) coupling in stoichiometric presence of copper, heteroaryl bromides require only catalytic amounts of copper(I) salts depending on the position of bromo substituents. Such selectivity coupled with ligand and solvent-free protocols appear promising from the viewpoint of ecology and economy and are more attractive as compared to the existing protocols.

Palladium-catalyzed selective amination of haloaromatics on KF-alumina surface

An efficient palladium-catalyzed amination, including polyaminations of aromatic bromides mediated on a surface of KF-alumina, is reported. The solvent-free one-pot protocol avoids the use of a strong base (sodium tert-butoxide) making it applicable to substrates containing a base-sensitive functional group. It proceeds without concomitant reductive bromination and provides access to selective amination of polyhaloaromatics.