25797-03-9

Basic information

• Product Name: 2-PHENYL-1H-PYRROLO[3,2-B]PYRIDINE
• Synonyms: 2-PHENYL-1H-PYRROLO[3,2-B]PYRIDINE;2-PHENYL-4-AZAINDOLE
• CAS NO: 25797-03-9
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.24
• Product Categories: Azaindoles
• Mol File: 25797-03-9.mol

Chemical Properties

• Melting Point: 235-242 °C
• Boiling Point: 407.2 °C at 760 mmHg
• Flash Point: 185.5 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.46±0.40(Predicted)
• CAS DataBase Reference: 2-PHENYL-1H-PYRROLO[3,2-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-1H-PYRROLO[3,2-B]PYRIDINE(25797-03-9)
• EPA Substance Registry System: 2-PHENYL-1H-PYRROLO[3,2-B]PYRIDINE(25797-03-9)

Safety Data

• Hazardous Substances Data: 25797-03-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Phenyl-1H-pyrrolo[3,2-b]pyridine is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to advancements in medicinal chemistry.
Used in Organic Compounds Synthesis:
As a versatile building block, 2-Phenyl-1H-pyrrolo[3,2-b]pyridine is employed in the synthesis of a wide range of organic compounds. Its incorporation into these molecules can enhance their chemical and physical properties, broadening their applications in various industries.
Used in Materials Science:
2-Phenyl-1H-pyrrolo[3,2-b]pyridine also has potential applications in the field of materials science. Its unique structure and properties can be leveraged to develop new materials with specific characteristics, such as improved stability, conductivity, or other desirable properties.

InChI:InChI=1/C13H10N2/c1-2-5-10(6-3-1)12-9-13-11(15-12)7-4-8-14-13/h1-9,15H

Upstream product

• 17738-11-3 (E)-1-phenyl-N-(pyridin-3-yl)ethan-1-imine 
• 288254-71-7 2-(phenyethynyl)-3-pyridinylamine 
• 945607-88-5 2-phenyl-1H-pyrrolo[3,2-b]pyridine 4-oxide 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 536-74-3 phenylacetylene 
• 462-08-8 pyridin-3-ylamine 
• 39856-58-1 3-amino-2-bromopyridine 
• 98-86-2 acetophenone 
• 98-81-7 1-bromovinylbenzene 
• 17738-11-3 C₁₃H₁₂N₂ 
• 3430-10-2 2-methyl-3-pyridinamine 
• 93-89-0 benzoic acid ethyl ester 
• 38240-21-0 2-mercapto-3-amino pyridine 

Downstream Products

• 1192159-95-7 tert-butyl 2-phenyl-1H-pyrrolo[3,2-b]pyridine-1-carboxylate 

Relevant articles and documents

Activation-free one-pot alkynylation–cyclization synthesis of 2-substituted 4-azaindoles and indoles

[Figure not available: see fulltext.] 2-Substituted 4-azaindoles and indoles are rapidly and efficiently prepared in an activation-free Pd-catalyzed alkynylation–cyclization sequence starting from 3-amino-2-bromopyridine or o-bromoaniline and terminal alkynes in a one-pot fashion.

Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

Aminopyridines are key building blocks for the synthesis of bioactive N-heterocyclic compounds such as azaindoles and imidazopyridines. However, the functionalization of aminopyridines is challenging, due to their electronic properties and coordination with metals. Herein we describe a reactivity study of aminopyridines under palladium-catalyzed reaction conditions. Several aminopyridines underwent a one-pot Pd-catalyzed C–N cross coupling reaction/C–H functionalization sequence affording azaindoles. The role of additives, ligands, and bases was investigated. This work consists of a platform for future studies on aminopyridines involving metal-catalyzed reactions and represents the first report on the direct conversion of non-halogenated aminopyridines into azaindoles via Pd-catalyzed C–H functionalization reactions.

Application of Fluorine- And Nitrogen-Walk Approaches: Defining the Structural and Functional Diversity of 2-Phenylindole Class of Cannabinoid 1 Receptor Positive Allosteric Modulators

Cannabinoid 1 receptor (CB1R) allosteric ligands hold a far-reaching therapeutic promise. We report the application of fluoro- and nitrogen-walk approaches to enhance the drug-like properties of GAT211, a prototype CB1R allosteric agonist-positive allosteric modulator (ago-PAM). Several analogs exhibited improved functional potency (cAMP, β-arrestin 2), metabolic stability, and aqueous solubility. Two key analogs, GAT591 (6r) and GAT593 (6s), exhibited augmented allosteric-agonist and PAM activities in neuronal cultures, improved metabolic stability, and enhanced orthosteric agonist binding (CP55,940). Both analogs also exhibited good analgesic potency in the CFA inflammatory-pain model with longer duration of action over GAT211 while being devoid of adverse cannabimimetic effects. Another analog, GAT592 (9j), exhibited moderate ago-PAM potency and improved aqueous solubility with therapeutic reduction of intraocular pressure in murine glaucoma models. The SAR findings and the enhanced allosteric activity in this class of allosteric modulators were accounted for in our recently developed computational model for CB1R allosteric activation and positive allosteric modulation.

Chelation-assisted C-S activation/cascade heteroannulation of pyridine-2-thione derivatives in Pd-catalyzed cross-coupling reaction with alkynes

Ortho-chelation assistance was proved to be crucial for the success of the desulfitative Sonogashira cross-coupling reaction of thioamide-type pyridine derivatives and alkynes. Corresponding alkynylated products were obtained with moderate to excellent yields. Thanks to this reaction, furo[3,2-b]pyridine and 1H-pyrrolo[3,2-b]pyridine derivatives were synthesized through a one-pot cross-coupling reaction/heteroannulation sequence.

Synthesis of Substituted 4-, 5-, 6-, and 7-Azaindoles from Aminopyridines via a Cascade C-N Cross-Coupling/Heck Reaction

A practical palladium-catalyzed cascade C-N cross-coupling/Heck reaction of alkenyl bromides with amino-o-bromopyridines is described for a straightforward synthesis of substituted 4-, 5-, 6-, and 7-azaindoles using a Pd2(dba)3/XPhos/t-BuONa system. This procedure consists of the first cascade C-N cross-coupling/Heck approach toward all four azaindole isomers from available aminopyridines. The scope of the reaction was investigated and several alkenyl bromides were used, allowing access to different substituted azaindoles. This protocol was further explored for N-substituted amino-o-bromopyridines.

Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes

A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.

Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles

An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles.

Pd-Catalyzed cascade reaction for the synthesis of 2-substituted indoles

An efficient cascade methodology toward the synthesis of 2-substituted indoles has been developed. The transformation proceeds via a palladium-catalyzed cross-coupling reaction of o-nitrobenzyl cyanides with boronic acids. The use of Fe as co-catalyst during the course of reaction employs significant enhancement in reaction rates. The developed protocol allows for the unprecedented use of arylboronic acids as coupling partners for constructing 2-substituted indoles. Georg Thieme Verlag Stuttgart · New York.

One-pot synthesis of azaindoles via palladium-catalyzed α-heteroarylation of ketone enolates

(Figure presented) A convenient, one-pot method for the construction of a variety of azaindoles using simple ketones and haloaminopyridines is described.

2-SUBSTITUTED AZAIN DOLES AND 2 SUBSTITUTED THIENOPYRROLES, THEIR PRECURSORS AND NOVEL PROCESSES FOR THE PREPARATION THEREOF

The present invention relates generally to processes for the chemical synthesis of azaindole and thienopyrrole compounds, in particular azaindole and thienopyrrole compounds that are substituted at the 2-position of the azaindole or thienopyrrole ring, an