13958-98-0

Basic information

• Product Name: 3-Bromo-4-cyanopyridine
• Synonyms: 3-BROMOPYRIDINE-4-CARBONITRILE;3-BROMO-4-CYANOPYRIDINE;3-Bromoisonicotinonitrile;3-bromoisonicotinonitrile(SALTDATA: FREE);3-Bromo-4-cyanopyridine,95%;2-Chloro-3-fluoro-1-nitrobenzene;4-Pyridinecarbonitrile,3-bromo-
• CAS NO: 13958-98-0
• Molecular Formula: C₆H₃BrN₂
• Molecular Weight: 183.01
• Product Categories: Pyridines;Heterocycle-Pyridine series
• Mol File: 13958-98-0.mol

Chemical Properties

• Melting Point: 92-94℃
• Boiling Point: 267.48 °C at 760 mmHg
• Flash Point: 115.568 °C
• Appearance: /
• Density: 1.726 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.48±0.18(Predicted)
• CAS DataBase Reference: 3-Bromo-4-cyanopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-4-cyanopyridine(13958-98-0)
• EPA Substance Registry System: 3-Bromo-4-cyanopyridine(13958-98-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• PackingGroup: III
• Hazardous Substances Data: 13958-98-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Bromo-4-cyanopyridine is used as a key intermediate in the synthesis of nicotinic receptor ligands, which are crucial for addressing diseases such as nicotinic addiction, neurodegenerative disorders, and cognitive impairments. Its unique structural features enable the development of targeted therapies for these conditions.
Used in the Synthesis of Cannabinoid Receptor Agonists:
3-Bromo-4-cyanopyridine is also utilized in the synthesis of orally bioavailable cannabinoid receptor 2 (CB2) agonists. These agonists have potential applications as analgesic and anti-inflammatory agents, offering alternative treatment options for pain management and inflammation-related conditions.

InChI:InChI:1S/C6H3BrN2/c7-6-4-9-2-1-5(6)3-8/h1-2,4H

Upstream product

• 626-55-1 3-Bromopyridine 
• 7677-24-9 trimethylsilyl cyanide 
• 1610416-94-8 3-bromoisonicotinaldehyde oxime 
• 927806-21-1 (Z)-3-bromoisonicotinaldehyde oxime 
• 13959-02-9 3-bromoisonicotinic acid 
• 100-48-1 pyridine-4-carbonitrile 
• 13958-99-1 3-bromopyridine-4-carboxamide 
• 3430-22-6 3-Bromo-4-methylpyridin 

Downstream Products

• 76006-17-2 1H-pyrazolo[3,4-c]pyridin-3-amine 
• 1246461-86-8 3-bromo-2-cyclohexylisonicotinonitrile 
• 1620076-13-2 C₁₃H₇BrF₂N₂O 
• 1613436-00-2 3-(4-methylphenyl)-2,6-naphthyridin-1-one 
• 1613435-99-6 4-cyano-3-(4-methylphenylethynyl)pyridine 
• 1373687-42-3 3-(2-(2-fluorophenyl)prop-1-en-1-yl)isonicotinonitrile 
• 1373686-80-6 N-(3-(1-amino-3-methyl-3,4-dihydro-2,6-naphthyridin-3-yl)-4-fluorophenyl)-5-cyanopicolinamide 
• 1373687-50-3 tert-butyl (3-(5-(5-cyanopicolinamido)-2-fluorophenyl)-3-methyl-3,4-dihydro-2,6-naphthyridin-1-yl)carbamate 
• 1373687-48-9 C₂₀H₂₃FN₄O₂ 
• 1373687-46-7 3-(2-fluoro-5-nitrophenyl)-3-methyl-3,4-dihydro-2,6-naphthyridin-1-amine 
• 1373687-44-5 3-(2-(2-fluorophenyl)prop-1-en-1-yl)isonicotinimidamide 
• 1290059-10-7 ethyl 2-((5-bromo-4-cyano-6-(cyclohex-2-en-1-yl)-3-iodopyridin-2-yl)methyl)acrylate 
• 1290059-09-4 3-bromo-2-(cyclohex-2-en-1-yl)-5-iodoisonicotinonitrile 
• 1310738-20-5 C₂₉H₃₃N₃O₂Si 

Relevant articles and documents

Efficient total syntheses of louisianins C and D

An efficient synthetic route for the preparation of louisianins C and D was developed starting with the commercially available 4-cyanopyridine. Louisianins C and D were synthesized in seven steps and with overall yields 22% and 20%, respectively, following a novel cyclization-decarboxylation sequence involving 4-bromo-6,7-dihydrocyclopenta[c]pyridin-5-one as the key intermediate.

C?H Cyanation of 6-Ring N-Containing Heteroaromatics

Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

N-(ARYLALKYL)-N'-PYRAZOLYL-UREA, THIOUREA, GUANIDINE AND CYANOGUANIDINE COMPOUNDS AS TRKA KINASE INHIBITORS

Compounds of Formula I or stereoisomers, tautomers, or pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein Ring A, Ring C, X, Ra, Rb, Rc, Rd and n are as defined herein, are inhibitors of TrkA kinase and are useful in the treatment of diseases which can be treated with a TrkA kinase inhibitor such as pain, cancer, inflammation/inflammatory diseases, neurodegenerative diseases, certain infectious diseases, Sjogren's syndrome, endometriosis, diabetic peripheral neuropathy, prostatitis or pelvic pain syndrome.

TANKYRASE INHIBITORS

The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.

NAPHTHYRIDINE DERIVATIVE

The present invention provides, for example, the following compound: wherein ring Z is pyridine or a carbocycle, each of which is substituted or unsubstituted, ring A is a carbocycle or a heterocycle, each of which is substituted or unsubstituted, R1

Selective and multiple functionalization of pyridines and alkaloids via Mg- and Zn-organometallic intermediates

Chemical equations presented. Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF3· OEt2. A full pyridi

Raf inhibitor compounds and methods of use thereof

Compounds of Formula I are useful for inhibiting Raf kinase and for treating disorders mediated thereby. Methods of using compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

Synthesis of ortho-substituted cyanopyridines through lithio intermediate trapping

Ortholithiation of 4-cyanopyridine using 2,2,6,6-tetramethylpiperidide (LiTMP) and trapping the lithio intermediate with electrophiles represents an efficient and straightforward access to ortho-substituted-4-cyanopyridines. The cyano group can be used as an ortho-directing group and allows the preparation of 3-halogeno-4-cyanopyridines. Reactivity of 2- and 3-cyanopyridines is also investigated and seems to give similar results.