119308-57-5

Usage

Uses

Used in Organic Synthesis:
Methyl 2,6-dibromopyridine-4-carboxylate is used as a building block in the organic synthesis industry for the preparation of various pharmaceuticals, agrochemicals, and functional materials. Its high reactivity and versatility in chemical reactions contribute to its value as an intermediate in the production of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 2,6-dibromopyridine-4-carboxylate is used as a key intermediate for the synthesis of drugs. Its unique structure and reactivity allow for the creation of new medicinal compounds with potential therapeutic applications.
Used in Agrochemical Industry:
Methyl 2,6-dibromopyridine-4-carboxylate is also utilized in the agrochemical industry as a precursor for the development of new pesticides and other agricultural chemicals, which can enhance crop protection and yield.
Used in Functional Materials:
In the production of functional materials, Methyl 2,6-dibromopyridine-4-carboxylate is used as a component in the synthesis of materials with specific properties, such as conductivity, magnetism, or catalytic activity, which can be applied in various high-tech applications.

InChI:InChI=1/C7H5Br2NO2/c1-12-7(11)4-2-5(8)10-6(9)3-4/h2-3H,1H3

Upstream product

• 67-56-1 methanol 
• 99-11-6 citrazinic acid 
• 2016-99-1 2,6-dibromoisonicotinic acid 

Downstream Products

• 223463-02-3 2,6-dibromo-4-(hydroxymethyl)pyridine 
• 2016-99-1 2,6-dibromoisonicotinic acid 
• 1092771-12-4 methyl 2-bromo-6-(3'-methoxyphenylamino)isonicotinamide 
• 1201674-86-3 4-(6-bromo-4-methoxycarbonylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester 
• 853029-93-3 2-bromo-6-methoxypyridine-4-carboxylic acid 
• 1251529-06-2 C₂₇H₃₃ClN₄O₄ 
• 1251529-42-6 C₂₄H₂₆BrClN₄O₄ 
• 1251528-82-1 C₂₅H₂₈BrClN₄O₄ 
• 1251528-69-4 C₂₆H₃₁BrClN₅O₃ 
• 1251529-04-0 C₂₉H₃₆ClN₅O₃ 
• 1372127-45-1 C₃₀H₃₇ClN₄O₄Si 
• 1434047-51-4 C₁₆H₁₉NO 
• 1434047-50-3 C₁₆H₁₇NO₂ 

Relevant academic research and scientific papers

"Super hybrid tridentate ligands": 4-substituted-2-(1-butyl-1H-1, 2,3-triazol-4-yl)-6-(1H-pyrazol-1-yl)pyridine ligands coordinated to Fe(ii) ions display above room temperature spin transitions

A series of novel "super hybrid tridentate ligands" based on (2-(1-butyl-1H-1,2,3-triazol-4-yl)-6-(1H-pyrazol-1-yl)pyridine (tpp) derivatives were synthesized. Their Fe(ii) complexes display around (T = 287 K) and above room temperature (T ? 375 K) spin transition temperatures.

Protein-Induced Change in Ligand Protonation during Trypsin and Thrombin Binding: Hint on Differences in Selectivity Determinants of Both Proteins?

Trypsin and thrombin, structurally similar serine proteases, recognize different substrates; thrombin cleaves after Arg, whereas trypsin cleaves after Lys/Arg. Both recognize basic substrate headgroups via Asp189 at the bottom of the S1 pocket. By crystal

6,6′-dibromo-4,4′-di(hexoxymethyl)-2,2′-bipyridine: A new solubilizing building block for macromolecular and supramolecular applications

Although brominated bipyridines and terpyridines are highly desirable synthetic building blocks for both ligand design and macro- or supramolecular applications, few such synthetic precursors have been reported that include much-needed solubilizing groups. Reported here is an inexpensive route to 2,6-dibromo-4-(hexoxymethyl)pyridine from citrazinic acid with an overall yield of 44% and its efficient conversion (60%) to 6,6′-dibromo-4,4′- di(hexoxymethyl)-2,2′-bipyridine via oxidative coupling.

Azacrown-attached meta-ethynylpyridine polymer: Saccharide recognition regulated by supramolecular device

Polymeric synthetic host 2, azacrown-attached 2,6-pyridylene ethynylene polymer, was investigated for its saccharide recognition and the additive effect of triethylene tetramine-trifluoroacetic acid; heteroallosteric effects were observed on the basis of CD and UV/Vis analyses, which indicated saccharide-dependent stabilization and destabilization of helical complexes by the formation of pseudopolyrotaxanes.

Highly active electrocatalytic CO2 reduction with manganese N-heterocyclic carbene pincer by para electronic tuning

Electronic tuning by para substitutions was explored to achieve a highly active manganese N-heterocyclic carbene pincer complex for the selective electrocatalytic reduction of CO2 to CO. [MnCNCOMe]BF4 (L2-Mn) bearing an electron-donating group (–OMe) showed high activity with 63 × catalytic current enhancement, average Faradaic efficiency of 104%, and a TOFmax value of 26,127 s?1, which is 127 times higher than that of unsubstituted [MnCNCH]Br (L1-Mn) reported previously. In contrast, the electron-withdrawing group (–COOMe) in [MnCNCCOOMe]PF6 (L3-Mn) inhibited the electrocatalytic activity. Ambient Br?nstic acid, however, suppressed the activity of L2-Mn probably due to the protonation of the –OMe group. These findings indicate a potential electronic tuning strategy to improved manganese N-heterocyclic carbene catalysts for CO2 reduction.

RSV INHIBITING 3-SUBSTITUTED QUINOLINE AND CINNOLINE DERIVATIVES

The invention concerns compounds of formula (I) having antiviral activity, in particular, having an inhibitory activity on the replication of the respiratory syncytial virus (RSV). The invention further concerns pharmaceutical compositions comprising these compounds and the compounds for use in the treatment of respiratory syncytial virus infection.

METHOD FOR SYNTHESIZING ENANIOMERICALLY PURE N-(PYRIDIN-4-YL)-2-HYDROXY-ALKYLAMIDE DERIVATIVES

The present invention relates to a novel process for preparing enantiomerically pure compounds of N-(pyrid-4-yl)-2-hydroxyalkylamide type corresponding to the general formula (C) below: and also to processes for preparing the reaction intermediates used i

Process Development and Crystallization in Oiling-Out System of a Novel Topical Antiandrogen

An efficient route to (S)-N-(2-bromo-6-methoxypyridin-4-yl)-2-hydroxy-2,4-dimethylpentanamide 1, a new topical antiandrogen, is described. The target compound has been manufactured on kilogram scale with an overall yield of 25% (HPLC purity 98.8% and >99% ee) from citrazinic acid. The key amide coupling between aminopyridine 4 and α-hydroxy-acid 6 was performed using a temporary protecting group to facilitate the acyl chloride formation. Aminopyridine 4 was manufactured from commercially available citrazinic acid via dibromide formation using phosphorus(V) oxybromide followed by mono SNAr reaction with sodium methoxide and a final Hofmann rearrangement. Enantiopure α-hydroxy-acid 6 was obtained using an enantioselective cyanosilylation followed by salt resolution with (S)-α-methyl benzylamine. The absolute configuration of compound 1 was determined with anomalous scattering and the final crystallization of API was performed after seeding a liquid-liquid mixture below the monotectic temperature and afforded a crystalline powder presenting a "desert rose" shape clusters.

First Structure-Activity Relationship of 17β-Hydroxysteroid Dehydrogenase Type 14 Nonsteroidal Inhibitors and Crystal Structures in Complex with the Enzyme

17β-HSD14 belongs to the SDR family and oxidizes the hydroxyl group at position 17 of estradiol and 5-androstenediol using NAD+ as cofactor. The goal of this study was to identify and optimize 17β-HSD14 nonsteroidal inhibitors as well as to disclose their structure-activity relationship. In a first screen, a library of 17β-HSD1 and 17β-HSD2 inhibitors, selected with respect to scaffold diversity, was tested for 17β-HSD14 inhibition. The most interesting hit was taken as starting point for chemical modification applying a ligand-based approach. The designed compounds were synthesized and tested for 17β-HSD14 inhibitory activity. The two best inhibitors identified in this study have a very high affinity to the enzyme with a Ki equal to 7 nM. The strong affinity of these inhibitors to the enzyme active site could be explained by crystallographic structure analysis, which highlighted the role of an extended H-bonding network in the stabilization process. The selectivity of the most potent compounds with respect to 17β-HSD1 and 17β-HSD2 is also addressed.

Inhibition of cancer-associated mutant isocitrate dehydrogenases: Synthesis, structure-activity relationship, and selective antitumor activity

Mutations of isocitrate dehydrogenase 1 (IDH1) are frequently found in certain cancers such as glioma. Different from the wild-type (WT) IDH1, the mutant enzymes catalyze the reduction of α-ketoglutaric acid to d-2-hydroxyglutaric acid (D2HG), leading to cancer initiation. Several 1-hydroxypyridin-2-one compounds were identified to be inhibitors of IDH1(R132H). A total of 61 derivatives were synthesized, and their structure-activity relationships were investigated. Potent IDH1(R132H) inhibitors were identified with Ki values as low as 140 nM, while they possess weak or no activity against WT IDH1. Activities of selected compounds against IDH1(R132C) were found to be correlated with their inhibitory activities against IDH1(R132H), as well as cellular production of D2HG, with R2 of 0.83 and 0.73, respectively. Several inhibitors were found to be permeable through the blood-brain barrier in a cell-based model assay and exhibit potent and selective activity (EC50 = 0.26-1.8 μM) against glioma cells with the IDH1 R132H mutation.