95881-83-7

Usage

Uses

Used in Chemical Synthesis:
3-Chloro-5-methoxypyridine is used as a chemical intermediate for the synthesis of more complex molecules. Its unique structure, featuring a chloro and methoxy group, allows it to be a versatile building block in the creation of various organic compounds.
Used in Laboratory Research:
3-Chloro-5-methoxypyridine is used as a research compound in controlled laboratory settings. Its properties and reactivity can be studied to understand its potential applications in the development of new chemical processes or as a component in advanced materials.
Used in Pharmaceutical Development:
3-Chloro-5-methoxypyridine is used as a potential precursor in the pharmaceutical industry for the development of new drugs. Its structure may offer specific interactions with biological targets, making it a candidate for further exploration in drug discovery and medicinal chemistry.

InChI:InChI=1/C6H6ClNO/c1-9-6-2-5(7)3-8-4-6/h2-4H,1H3

Upstream product

• 2457-47-8 3,5-dichloropyridine 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 74115-12-1 5-chloropyridin-3-ol 

Downstream Products

• 214976-36-0 3-chloro-5-methoxyisonicotinic acid 
• 214976-39-3 3-(5-Chloro-2-fluoro-benzyl)-5-methoxy-isonicotinic acid 
• 214976-38-2 3-(5-Chloro-2-fluoro-benzyl)-5-methoxy-isonicotinic acid methyl ester 
• 64436-92-6 3-amino-5-methoxypyridine 

Relevant academic research and scientific papers

Creating an antibacterial with in vivo efficacy: Synthesis and characterization of potent inhibitors of the bacterial cell division protein FTSZ with improved pharmaceutical properties

3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure-activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.

New ligands with affinity for the α4β2 subtype of nicotinic acetylcholine receptors. Synthesis, receptor binding, and 3D-QSAR modeling

A new series of piperazines, diazepanes, diazocanes, diazabicyclononanes, and diazabicyclodecanes with affinity for the α4β 2 subtype of nicotinic acetylcholine receptors were synthesized on the basis of results from a previous computational study. A predictive 3D-QSAR model was developed using the GRID/GOLPE approach (R2 = 0.94, Q 2 = 0.83, SDEP = 0.34). The SAR was interpreted in terms of contour maps of the PLS coefficients and in terms of a homology model of the α4β2 subtype of the nicotinic acetylcholine receptors. The results reveal that hydrogen bonding from both hydrogens on the protonated amine and from the pyridine nitrogen to a water molecule as well as van der Waals interactions between the substituent bearing the protonated amine and the receptor is of importance for ligand affinity. The combination of 3D-QSAR and homology modeling proved successful for the interpretation of structure-affinity relationships as well as the validation of the individual modeling approaches.

The reaction of 5-chloro derivatives of 3-pyridinol and 3- methoxypyridine with various amines under aryne-forming conditions

The reactions of 5-chloro-3-pyridinol (1) and 5-chloro-3-methoxy- pyridine (6) with various lithium amides (2') in THF or free amine solvent (2) have been studied and the results reported herein. In most cases, 5- aminated products were exclusively formed

Synthesis of hydroxy-substituted aza-analogues of antitumor anthrapyrazoles

Synthetic routes have been developed which lead to ring-hydroxylated aza-analogues of antitumor anthrapyrazoles, namely, 2,5- bis[(aminoalkyl)amino] substituted 10-hydroxyindazo[3,4-fg]isoquinolin- 6(2H)-ones 1 and 7-hydroxyindazolo[4,3-gh]isoquinolin-6(2H)-ones 2. The regiospecific synthesis of 6,9-dihalo-4-hydroxybenz[g]isoquinolines 3 and 4 has been accomplished. Intermediate 3 was constructed in a multistep process involving Diels-Alder chemistry of benzolacrylates whereas 4 was assembled using Ni(II) mediated coupling of methyl 3-chloro-5-methoxyisonicotinate (15b) with the organic zinc reagent 18 derived from 2-fluoro-5-chlorobenzyl bromide (17). After protection of the hydroxy group with a p-methoxybenzyl moiety, the different nucleofugacities of the leaving groups present in 10 and 20 allowed sequential displacements by substituted hydrazines and amines, respectively, to lead to the desired p-methoxybenzyl protected analogues 12 and 22. Deprotection led to the side arm modified compounds 1 and 2. The displacements of 21a and 21b with N,N-dimethylethylenediamine also led to the tri[(aminoalkyl)amino]substituted analogues 23s and 23b, respectively, which arose from further S(N)Ar substitutions of the p-methoxybenzyloxy group.

NEW REACTIONS OF PYRIDINES AND TOTAL SYNTHESIS OF THE FUNGAL TOXIN ORELLANINE

Dihalogenated pyridines react easily with sulphur nucleophiles, in dipolar aprotic solvents (DMF), to afford the products of mono- or of bis-substitution depending on the experimental conditions.On the contrary, with oxygen nucleophiles the bis-substituted products can be obtained only with some particular substrates.A new and efficient procedure to effect the homo-coupling of halogenoarenes will be presented.This reaction, wich occurs under the influence of low-valent nickel complexes, allowed us to effect the total synthesis of Orellanine, the lethal toxin of Cortinarius orellanus mushroom, as well as the syntheses of its decompositionproducts Orellinine and Orelline.The chemical properties of these three products and their behaviour towards UV irradiation will be presented and discussed.