55052-28-3

Basic information

• Product Name: 4-Chloro-7-azaindole
• Synonyms: IFLAB-BB F2108-0145;1H-PYRROLO[2,3-B]PYRIDINE, 4-CHLORO-;4-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE;4-CHLORO-7-AZAINDOLE;4-Chloro-1H-pyrrolo[2,3-b]pyridin;4-Chloro-1H-pyrrolo[2,3-β]pyridine;4-Chloro-7-azaindole ,97%;4-Chloro-7-azaindole,4-Chloro-1H-pyrrolo[2,3-b]pyridine
• CAS NO: 55052-28-3
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• EINECS: 1592732-453-0
• Product Categories: Various Intermediates;Heterocycles;Indole Derivatives;Intermediates;Azaindoles;Heterocycle-Indole series
• Mol File: 55052-28-3.mol

Chemical Properties

• Melting Point: 174-176°C
• Appearance: /
• Density: 1.425 g/cm³
• Refractive Index: 1.703
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.98±0.40(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Chloro-7-azaindole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-7-azaindole(55052-28-3)
• EPA Substance Registry System: 4-Chloro-7-azaindole(55052-28-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 55052-28-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-azaindole is used as a key intermediate for drug discovery research, particularly in the synthesis of 7-azaindole derivatives and synthetic cytokinin analogues. These compounds have potential applications in the development of new drugs for various medical conditions.
As a crucial component in the synthesis of pharmaceutical compounds, 4-Chloro-7-azaindole contributes to the advancement of drug discovery and the creation of novel therapeutic agents. Its versatility in chemical reactions and compatibility with various synthetic pathways make it an essential tool in the pharmaceutical industry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 71, p. 4021, 2006 DOI: 10.1021/jo0602571

InChI:InChI=1/C7H5ClN2/c8-6-2-4-10-7-5(6)1-3-9-7/h1-4H,(H,9,10)

Upstream product

• 55052-24-9 1H-Pyrrolo[2,3-b]pyridine-7-oxide 
• 124-63-0 methanesulfonyl chloride 
• 74420-00-1 4-amino-1H-pyrrolo<2,3-b>pyridine 
• 271-63-6 7-Azaindole 
• 74420-18-1 7-Hydroxy-1H-pyrrolo<2,3-b>pyridinium m-chlorobenzoate 
• 744209-63-0 1-(benzenesulfonyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine 
• 74420-06-7 4-nitro-1H-pyrrolo<2,3-b>pyridine 7-oxide 
• 1033809-58-3 1H-pyrrolo[2,3-b]pyridine 7-oxide hydrochloride 

Downstream Products

• 74420-04-5 1-Benzyl-4-Chloro-1H-pyrrolo<2,3-b>pyridine 
• 122379-57-1 1-p-Tolyl-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 122379-53-7 1-(4-Chloro-phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 122379-59-3 1-(4-Methoxy-phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 122379-55-9 1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-4-amine 
• 122379-49-1 4-amino-1-phenyl-1H-pyrrolo<3,2-c>pyridine 
• 122379-64-0 4-(N-methylanilino)-1H-pyrrolo<2,3-b>pyridine 
• 122379-51-5 1-(4-Fluoro-phenyl)-1H-pyrrolo[3,2-c]pyridin-4-ylamine 
• 102839-56-5 4-amino-1-methyl-1H-pyrrolo<3,2-c>pyridine 
• 122379-60-6 4-(dimethylamino)-1H-pyrrolo<2,3-b>pyridine 
• 122379-62-8 (1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-acetic acid ethyl ester 
• 74420-05-6 1-Methyl-4-chloro-1H-pyrrolo<2,3-b>pyridine 
• 122379-63-9 4-methoxy-1H-pyrrolo<2,3-b>pyridine 
• 74420-03-4 4-Chloro-1H-pyrrolo<2,3-b>pyridine 7-oxide 

Relevant articles and documents

4-Amino-pyrrolopyridine-5-carboxamide: A novel scaffold for JAK1-selective inhibitors

Despite a high level of interest in selective Janus kinase 1 (JAK1) inhibitors and their potential for the treatment of inflammatory diseases such as rheumatoid arthritis (RA), only a few such inhibitors have been reported to date. In this study, a novel 4-amino-1H-pyrrolo[2,3-b]pyridine-5-carboxamide scaffold was designed through structural modification of the potent JAK1-selective inhibitor, C2-methyl imidazopyrrolopyridine. Among the series studied, the 4-(2-aminoethyl)amino-pyrrolopyridine derivative, 2j, exhibited a significant 24.7-fold JAK1/JAK2 selectivity along with reasonable inhibitory activity against JAK1 (IC50=2.2 μM). The noticeable JAK1-selectivity of 2j was then tackled through a molecular docking study, which showed that the aminoethyl functionality of 2j is well positioned to discriminate the subtle but significant difference in the size of the ligand binding sites between JAK1 and JAK2.

DERIVATIVES OF AN FGFR INHIBITOR

The present disclosure relates to derivatives (e.g., hydroxyl, keto, glucuronide, sulfonic acid, and deuterated) of a Fibroblast Growth Factor Receptors (FGFR) inhibitor, including methods of preparation thereof, and intermediates in the preparation thereof, which are useful in the treatment of FGFR mediated disease such as cancer.

Design and synthesis of 7-azaindole derivatives and their antitumor and analgesic activities

To develop effective anti-tumor and analgesic drugs, a series of novel 7-azaindole derivatives were designed and synthesized through a four-step reaction. 18 target compounds were obtained and characterized through Nuclear Magnetic Resonance and High Resolution Mass Spectrometry. Their anti-proliferative activities and analgesic effect were evaluated. When the 1-position was a methylsulfonyl group and the 5-position was a nitro group, compound 4f demonstrated the best activity. Furthermore, there was a dramatic difference between the IC50 values of compound 4f in tumor and in healthy cell line. The IC50 values of compound 4f in MCF7 breast cancer cell line was 5.781 μmol/L and 8.077 μmol/L in HepG2 hepatoma carcinoma cell line, but more than 100 μmol/L in HL7702 liver cell line. Preliminary results showed that compounds 3a, 3g and 4i had significant analgesic effects in mice, which were stronger than aspirin. These compounds have good prospects for new drug development.

Method for synthesizing Meriolin

The invention belongs to the field of medicinal chemistry, and concretely relates to a method for synthesizing Meriolin. The method comprises the following steps: 7-azaindole used as a raw material undergoes an oxidation reaction to generate an intermediate 2; the intermediate 2 undergoes a halogenations reaction to generate an intermediate 3; the intermediate 3 is subjected to a Friedel-Crafts acylation to generate an intermediate 4; and the amino group of the intermediate 4 is protected to obtain an intermediate 5, the intermediate 5 undergoes an alkylation reaction to generate an intermediate 6, and the intermediate 6 is cyclized to obtain the target products Merilin 10 and Meriolin 7. The method adopting the inexpensive 7-azaindole as the raw material has the advantages of simple operation steps, mild reaction conditions, avoiding the use of CO, high temperature, high pressure and expensive Pd catalytic reagent and hazardous chemicals, obtaining of the Meriolin 10 and Meriolin 7 ata high yield, and provision of a new idea for the synthesis of Meriolins series new derivatives.

Synthesis and structure?activity?relationship of 3,4?Diaryl?1H?pyrrolo[2,3?b]pyridines as irreversible Inhibitors of mutant EGFR?L858R/T790M

The epidermal growth factor receptor (EGFR) is a well?validated drug target for the treatment of non?small cell lung cancer. Here we present an optimization approach and preliminary structure?activity relationship for 1H?pyrrolo[2,3?b]pyridines as covalent irreversible mutant EGFR inhibitors. We synthesized a focused library to investigate the effect of different aromatic substituents in the 4?position of this scaffold, interacting with the gatekeeper. We determined the activity of the synthesized compounds mutant EGFR enzyme assays and determined the selectivity over the wild type.

SOLID FORMS OF AN FGFR INHIBITOR AND PROCESSES FOR PREPARING THE SAME

The present disclosure relates to 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one, solid forms and polymorphs thereof, methods of preparation thereof, and intermediates in the preparation thereof, which are useful in the treatment of the FGFR-associated or mediated diseases such as cancer.

Pyrrolo[3,2-c]pyridine derivatives with potential inhibitory effect against FMS kinase: in vitro biological studies

A series of eighteen pyrrolo[3,2-c]pyridine derivatives were tested for inhibitory effect against FMS kinase. Compounds 1e and 1r were the most potent among all the other tested analogues (IC50 = 60 nM and 30 nM, respectively). They were 1.6 and 3.2 times, respectively, more potent than our lead compound, KIST101029 (IC50 = 96 nM). Compound 1r was tested over a panel of 40 kinases including FMS, and exerted selectivity against FMS kinase. It was further tested against bone marrow-derived macrophages (BMDM) and its IC50 was 84 nM (2.32-fold more potent than KIST101029 (IC50 = 195 nM)). Compound 1r was also tested for antiproliferative activity against a panel of six ovarian, two prostate, and five breast cancer cell lines, and its IC50 values ranged from 0.15–1.78 μM. It possesses also the merit of selectivity towards cancer cells than normal fibroblasts.

A new synthetic process of the pyrrole compounds and the use of the anti-tumor effect (by machine translation)

The present invention discloses a new synthetic process of the pyrrole compounds and the use of the anti-tumor effect, and in particular relates to compounds 1 - benzenesulfonyl - 4 - chloro - 5 - nitro - 1 H - pyrrolo [2, 3 - b] pyridine, hydrate and its salt of new synthetic process and the use of the anti-tumor effect, this synthesis process takes 1 H - pyrrolo [2, 3 - b] pyridine as the starting material, after chloro-, prepared by acylation reaction such as 1 - benzenesulfonyl - 4 - chloro - 5 - nitro - 1 H - pyrrolo [2, 3 - b] pyridine, hydrate and its salt, provides a simple operation, high yield of the new process, the preparation method is simple, mild reaction conditions, at the same time the compound anti-tumor activity is prominent, little toxicity to normal cell, is favorable to its anti-tumor field widely popularized. (by machine translation)

Discovery of N-substituted 7-azaindoles as PIM1 kinase inhibitors – Part I

Novel N-substituted azaindoles have been discovered as PIM1 inhibitors. X-ray structures have played a significant role in orienting the chemistry effort in the initial phase of hit confirmation. Disclosure of an unconventional binding mode for 1 and 2, as demonstrated by X-ray crystallography, is presented and was an important factor in selecting and advancing a lead series.

Production technology for 4-chlorine-7-azaindole

The invention relates to a production technology for 4-chlorine-7-azaindole. The technology comprises the following steps: adding N-oxo-7-azaindole and tetrahydrofuran into a reaction flask, opening and stirring; adding methylsulfonyl chloride while stirring and naturally releasing heat; heating, preserving heat and stirring till completely consuming the raw materials; after completely consuming the raw materials, reducing temperature to 15 DEG C, controlling the temperature within 15 DEG C-20 DEG C, dropwise adding sodium hydroxide aqueous solution, separating liquid for separating aqueous phase and washing with water; spin-steaming and removing dissolvent from organic phase, thereby acquiring a dark brown solid; using dichloromethane for pulping, thereby acquiring a faint yellow solid, namely, 4-chlorine-7-azaindole. The methylsulfonyl chloride is simultaneously used as a chloride agent and a water removing agent, so that the cost is saved and the operation difficulty is reduced; the special solubility property of the product is utilized, the dichloromethane with excellent solubility is used for pulping and purifying and the effect is excellent; the production technology is easily controlled and is convenient for industrialization and the product is high in purity.