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
• Article Data: 18

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

General Description

2-Phenyl-1H-pyrrolo[3,2-b]pyridine is a chemical compound with the molecular formula C14H10N2. It is a heterocyclic compound consisting of a pyrrole ring fused to a pyridine ring, with a phenyl group attached to the pyrrole ring. 2-Phenyl-1H-pyrrolo[3,2-b]pyridine is used in the synthesis of pharmaceuticals and organic compounds, and it also has potential applications in the field of materials science. Its unique structure and properties make it a valuable building block for the preparation of diverse organic molecules, and it is of interest to researchers in medicinal chemistry and chemical synthesis.

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 
• 627510-86-5 2-phenyl-1H-pyrrolo[3,2-b]pyridin-1-ol 
• 945607-88-5 2-phenyl-1H-pyrrolo[3,2-b]pyridine 4-oxide 
• 947330-58-7 3-nitro-2-(phenylethynyl)pyridine 
• 945607-69-2 2-(2,2-dichlorovinyl)-pyridin-3-ylamine 
• 945607-84-1 C₁₅H₁₂Cl₂N₂O₂ 
• 945607-87-4 [2-(2,2-dichlorovinyl)-1-oxypyridin-3-yl]-carbamic acid benzyl ester 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 536-74-3 phenylacetylene 
• 627510-84-3 3-nitro-2-[(E)-2-phenylethenyl]pyridine 
• 627510-85-4 N-{2-[(E)-2-phenylethenyl]pyridin-3-yl}hydroxylamine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 462-08-8 pyridin-3-ylamine 

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.

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.

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.