70201-43-3

Basic information

• Product Name: 3-BROMO-4-FORMYLPYRIDINE
• Synonyms: 3-Bromoisonicotinaldehyde ,98%;3-Bromopyridine-4-carboxaldehyde ,98%;5-BroMopyridine-4-carboxaldehyde;CHEMBRDG-BB 4003258;3-BROMO-4-PYRIDINECARBOXALDEHYDE;3-BROMO-4-FORMYLPYRIDINE;3-BROMO-PYRIDINE-4-CARBALDEHYDE;3-BROMOPYRIDINE-4-CARBOXALDEHYDE
• CAS NO: 70201-43-3
• Molecular Formula: C₆H₄BrNO
• Molecular Weight: 186.01
• EINECS: -0
• Product Categories: C1 to C6;C5 to C6;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Organic Building Blocks;NULL;pharmacetical;Aldehydes;Pyridines;Pyridine;Building Blocks;Halogenated;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 70201-43-3.mol

Chemical Properties

• Melting Point: 81-82 °C(lit.)
• Boiling Point: 246.2 °C at 760 mmHg
• Flash Point: 102.7 °C
• Appearance: /
• Density: 1.683 g/cm³
• Vapor Pressure: 0.0275mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 0.90±0.18(Predicted)
• CAS DataBase Reference: 3-BROMO-4-FORMYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-FORMYLPYRIDINE(70201-43-3)
• EPA Substance Registry System: 3-BROMO-4-FORMYLPYRIDINE(70201-43-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 70201-43-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-BROMO-4-FORMYLPYRIDINE is used as a reagent for the synthesis of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles agonists. These agonists interact with the G-protein-coupled bile acid receptor 1 (TGR5), which can induce insulin secretion. This interaction may be utilized as a potential treatment for diabetes mellitus, offering a novel approach to managing blood sugar levels in diabetic patients.

InChI:InChI=1/C6H4BrNO/c7-6-3-8-2-1-5(6)4-9/h1-4H

Upstream product

• 626-55-1 3-Bromopyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 872-85-5 pyridine-4-carbaldehyde 
• 865449-16-7 3-bromo-4-(dibromomethyl)pyridine 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 108-18-9 diisopropylamine 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 107-31-3 Methyl formate 
• 2591-86-8 N-Formylpiperidine 
• 663170-90-9 3-bromo-4-(diethoxymethyl)pyridine 

Downstream Products

• 222167-48-8 3-(2-phenylethynyl)pyridine-4-carboxaldehyde 
• 263024-69-7 3-bromo-4-(cyclohex-2-enylmethanol)pyridine 
• 606123-02-8 2-[3,5-di-iso-propyl-6-(2,2,2-trifluoroethoxy)benzene]-4-formylpyridine 
• 650628-88-9 3-methylthioisonicotinaldehyde 
• 941608-71-5 C₁₂H₁₂BrNO₄ 
• 953805-52-2 C₁₂H₁₀BrNO₃ 
• 941608-87-3 C₂₀H₂₁F₂NO₂S 
• 870235-32-8 4-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester 
• 871583-22-1 methyl 4-(methylthio)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate 

Relevant articles and documents

Pyridine analogues of spirocyclic σ1 receptor ligands

Spirocyclic benzopyrans 2 interact with high affinity and selectivity with σ1 receptors. Bioisosteric replacement of the benzene ring of the benzopyran substructure with the electron rich thiophene ring (3) led to increased σ1 affinity. Herein the synthesis and pharmacological evaluation of electron deficient pyridine bioisosteres 4 are reported. Homologation of the aldehyde 6 to afford the pyridylacetaldehyde derivative 8 was performed by a Wittig reaction. Bromine lithium exchange of the bromopyridine 8, addition to 1-benzylpiperidin-4-one and cyclization led to the spirocyclic pyrranopyridine 10. Hydrogenolytic removal of the N-benzyl moiety of 10 provided the secondary amine 11, which allowed the introduction of various N-substituents (12a-d). Cyclization of the hydroxy acetal 9 with HCl led to various modifications of the substituent in 3′-position. Generally the σ1 affinity of the pyridine derivatives is reduced compared with those of the benzene and thiophene derivatives 2 and 3. However, the relationships between the structure and the σ1 affinity follow the same rules as for the benzene and thiophene derivatives. The most promising σ1 ligand within this class of compounds is the pyranopyridine 15 with a double bond in the pyran ring revealing a Ki-value of 4.6 nM and a very high selectivity (>217-fold) over the σ2 subtype.

Synthesis of a new series of potent inhibitors of thromboxane A2 biosynthesis

The pyridino prostanoids 9, 12 and 14 have been synthesized (in racemic form) and have been found to be effective inhibitors of the biosynthesis of thromboxane A2 in human platelets (IC50 1-3 μM).

One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes

The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.

Transition-Metal-Free Oxidation of Benzylic C-H Bonds of Six-Membered N-Heteroaromatic Compounds

A novel oxidation of benzylic C-H bonds for the synthesis of diverse six-membered N-heteroaromatic aldehydes and ketones has been developed. The obvious advantages of this approach are the simple operation, mild reaction conditions, and without use of toxic reagent and transition metal. The present method should provide a useful access for the synthesis and modification of N-heterocycles.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof:wherein Y1 is of formula (?) or formula (y):Ring Y is a 5- to 6-membered heteroaryl ring; and V4, V5, Rx, x, y, and n are as defined herein. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

THIENO[3,2-D]PYRIMIDINE-6-CARBOXAMIDES AND ANALOGUES AS SIRTUIN MODULATORS

Provided herein are novel substituted thieno[3,2-d]pyrimidine-6-carboxamide sirtuin inhibitors and methods of use thereof. The sirtuin inhibitors may be used for inhibiting a sirtuin-mediated biological process, and, e.g. for treating and/or preventing diseases and disorders including, but not limited to cancer, neurodegenerative disease and inflammation. Also provided herein are pharmaceutical compositions comprising these sirtuin inhibitors and compositions comprising a sirtuin inhibitor in combination with another therapeutic agent.

Synthesis and σ receptor affinity of regioisomeric spirocyclic furopyridines

In order to investigate systematically the effect of the position of the pyridine N-atom on the σ1 receptor affinity four regioisomeric furopyridines 2a-d were synthesized and pharmacologically evaluated. The key steps of the synthesis comprise bromine/lithium exchange at regioisomeric bromopyridinecarbaldehyde acetals 7a-d, subsequent addition to 1-benzylpiperidin-4-one and cyclization. The regioisomeric acetals 7a-d were obtained either by o-metalation of bromopyridines 5b and 5c or by oxidation of bromopicolines 3a and 3d. In radioligand binding studies the regioisomeric furopyridines 2a-d showed 7- to 12-fold lower σ1 affinity than the benzofuran analog 1. The reduced σ1 affinity of the furopyridines 2a-d is explained with the reduced electron density of the pyridine ring. Since the four regioisomeric furopyridines show almost the same σ1 affinity (Ki = 4.9-10 nM), a directed interaction of the pyridine N-atom with the receptor protein can be excluded.

Copper(I) salt/PEG-400 catalysis in one-pot direct synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines

2-Bromobenzaldehydes are condensed and cyclized with arylhydrazines (or their hydrochlorides) in PEG-400 at 110 °C in the presence of a catalytic amount of a copper(I) salt along with a base to give 1-aryl-1H-indazoles in high yields. Copyright 2013 John Wiley & Sons, Ltd. Condensation of 2-bromobenzaldehydes with arylhydrazines (or their hydrochlorides) followed by C-N bond formation in PEG-400 in the presence of a copper(I) salt along with a base affords 1-aryl-1H-indazoles. Copyright

Expeditious synthesis of cis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo- [3,2h]isoquinoline/[2,3-f]quinoline via azomethine ylide-alkene [3+2] cycloaddition

Expeditious syntheses of cis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo- [3,2h]isoquinoline/[2,3-f]quinoline have been developed. The syntheses started with commercially available materials and afforded excellent overall yields in straightforward steps. Intramolecular azomethine ylide-alkene [3+2] cycloaddition is the key step in the construction of these pyrroloisoquinoline and pyrroloquinoline scaffolds. This route is much more atom-economic than those reported in the literature and is appropriate for scale-up synthesis.

Synthesis of 1-phenyl- and 1-pyridyl-3-pyridoazepines by reductive cyclization of diarylacetonitriles

Several pyrido[2,3-d]azepines and pyrido[3,4-d]azepines, novel aza analogs of the pharmacologically relevant 1-aryl-3-benzazepines, were synthesized by assembling the azepine ring by reductive cyclization of (2-methoxyvinyl)pyridinyl(aryl)acetonitrile derivatives, which were easily derived from contiguously substituted bromo(2-methoxyvinyl)pyridines and the corresponding arylacetonitriles.