69872-17-9

Basic information

• Product Name: 4-bromo-1H-pyrrolo[2,3-c]pyridine
• Synonyms: 4-bromo-1H-pyrrolo[2,3-c]pyridine;4-Bromo-6-azaindole;1H-PYRROLO[2,3-C]-PYRIDINE,4-BROMO-;4-BroM-6-azaindol;4-broMo-1H-pyrrolo[2,3-c]pyridin
• CAS NO: 69872-17-9
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.035
• EINECS: 200-258-5
• Mol File: 69872-17-9.mol

Chemical Properties

• Melting Point: 188-189℃
• Boiling Point: 337.619 °C at 760 mmHg
• Flash Point: 157.986 °C
• Appearance: /
• Density: 1.770
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: 2-8°C(protect from light)
• PKA: 13.73±0.40(Predicted)
• CAS DataBase Reference: 4-bromo-1H-pyrrolo[2,3-c]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-1H-pyrrolo[2,3-c]pyridine(69872-17-9)
• EPA Substance Registry System: 4-bromo-1H-pyrrolo[2,3-c]pyridine(69872-17-9)

Safety Data

• RIDADR: UN2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 69872-17-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-Bromo-1H-Pyrrolo[2,3-c]Pyridine is utilized as a key building block for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Organic Chemistry Research:
As a reagent, 4-Bromo-1H-Pyrrolo[2,3-c]Pyridine is employed in organic chemistry reactions, particularly for the formation of carbon-carbon and carbon-heteroatom bonds. This enhances the synthesis of complex organic molecules and contributes to the advancement of organic chemistry.
Used in Materials Science:
4-Bromo-1H-Pyrrolo[2,3-c]Pyridine has potential applications in materials science, where its unique properties can be harnessed to develop new materials with specific characteristics for various applications.
Used as a Precursor for Novel Organic Compounds:
4-Bromo-1H-Pyrrolo[2,3-c]Pyridine also serves as a precursor for the synthesis of novel organic compounds, expanding the scope of organic chemistry and providing new avenues for research and development in the field.

InChI:InChI=1/C7H5BrN2/c8-6-3-9-4-7-5(6)1-2-10-7/h1-4,10H

Upstream product

• 69872-14-6 diethyl 2-(3-bromo-5-nitro-4-pyridyl)propanedioate 
• 5435-54-1 4-hydroxy-3-nitropyridine 
• 69872-15-7 3-bromo-4-methyl-5-nitropyridine 
• 31872-63-6 3-bromo-4-chloro-5-nitropyridine 
• 31872-65-8 3-bromo-5-nitropyridin-4-ol 
• 69872-16-8 [2-(3-bromo-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine 
• 1258875-12-5 (E)-2-(3-bromo-5-nitro-4-pyridinyl)-N,N-dimethylethenamine 

Downstream Products

• 850892-97-6 tert-butyl 4-bromo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate 
• 1312368-90-3 B-1H-pyrrolo[2,3-c]pyridin-4-ylboronic acid 
• 1190310-26-9 3-iodo-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile 
• 1578264-56-8 C₁₈H₁₆FN₃O₃ 
• 1578264-57-9 C₁₈H₁₆FN₃O₃ 
• 1578264-53-5 C₁₈H₁₆FN₃O₃ 

Relevant articles and documents

A Journey through Hemetsberger–Knittel, Leimgruber–Batcho and Bartoli Reactions: Access to Several Hydroxy 5- and 6-Azaindoles

The preparation of various 5- and 6-azaindoles, heterocyclic structures that are frequently part of molecules in clinical development, and their monohydroxy analogues were described. Different strategies, relying on the de novo pyrrole ring formation, were investigated and, thanks to Hemetsberger–Knittel, Bartoli and Leimgruber–Batcho approaches, 4- and 7-monohydroxy 5- and 6-azaindoles were obtained. The crucial introduction of the oxygen atom was carried out from halogen derivatives, using nucleophilic substitution reactions under basic conditions with or without a copper catalyst. Some preliminary oxidation reactions have shown that it was yet not possible to synthesize the azaquinone indole structure from monohydroxy azaindole, using molecular oxygen in the presence of salcomine as a catalyst.

AZAINDOLE CARBOXAMIDE COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS

Provided herein are compounds of Formula (I) and Formula (II): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of tuberculosis.

1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators

We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

Azaindolines: Derisking the indoline structural alert

4-Substitued azaindolines, which are isosteres of indolines, are useful synthetic building blocks that reduce the risk of bioactivation induced idiosyncratic toxicity have been prepared. Multigram routes to 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-4-triflate 16, 2,3-dihydro-1H-pyrrolo[2,3- b]pyridine-4-carbonitrile 20 and 4-chloro-2,3-dihydro-1H-pyrrolo[2,3-d] pyridazine 30 are outlined.

INDAZOLECARBOXAMIDE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF MALARIA

The invention relates to methods of treating or preventing malaria which comprises administering to a patient in need thereof, an effective amount of a 1H-indazole-3-carboxamide derivative of general formula (I), in the form of a base or of an addition salt with an acid, or in the form of a hydrate or of a solvate of said base or acid addition salt.

Indazolecarboxamide derivatives, preparation and use thereof as CDK1, CDK2 and CDK4 inhibitors

Compound corresponding to general formula (I): [image] in which, R1 represents a hydrogen or halogen atom, an NH2, NHR2, NHCOR2, NO2, CN, CH2NH2 and CH2NHR2; or alternatively R1 represents an optionally substituted phenyl or an optionally substituted heteroaromatic group; Ar represents an optionally substituted phenyl group or an optionally substituted heteroaromatic group; n represents 0, 1, 2 or 3; in the form of a base, of an addition salt with an acid, of a hydrate or of a solvate. Application in therapy.

3,5 Disubstituted indazole compounds with nitrogen-bearing 5-membered heterocycles, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation

3,5 disubstituted indazole compounds with substituted nitrogen bearing 5-membered heterocycles in the 3-position that modulate and/or inhibit cell proliferation, such as the activity of protein kinases are described. These compounds and pharmaceutical com