147621-19-0

Basic information

• Product Name: 6-PYRIDIN-3-YL-1H-INDOLE
• Synonyms: 6-PYRIDIN-3-YL-1H-INDOLE
• CAS NO: 147621-19-0
• Molecular Formula: C13H10N2
• Molecular Weight: 194.23
• Mol File: 147621-19-0.mol

Chemical Properties

• Boiling Point: 420.1 °C at 760 mmHg
• Flash Point: 192.9 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 7.07E-07mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-PYRIDIN-3-YL-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-PYRIDIN-3-YL-1H-INDOLE(147621-19-0)
• EPA Substance Registry System: 6-PYRIDIN-3-YL-1H-INDOLE(147621-19-0)

Safety Data

• Hazardous Substances Data: 147621-19-0(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
6-PYRIDIN-3-YL-1H-INDOLE is used as a potential compound for the development of new drugs, given its indole core and pyridine ring, which are common structural elements in many biologically active molecules. Its unique structure may allow for the design of novel therapeutic agents with specific target interactions.
Used in Materials Science:
6-PYRIDIN-3-YL-1H-INDOLE is used as a building block for the synthesis of new materials with potential applications in various fields, such as electronics, photonics, or catalysis. The indole and pyridine rings in its structure may contribute to the formation of novel materials with unique properties and functions.

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

Upstream product

• 626-55-1 3-Bromopyridine 
• 147621-18-9 6-indolylboronic acid 
• 17422-33-2 6-chloroindole 
• 1692-25-7 3-pyridylboronic acid 
• 626-60-8 3-Chloropyridine 
• 52415-29-9 6-bromo-1H-indole 

Relevant articles and documents

Identification of an Indazole-Based Pharmacophore for the Inhibition of FGFR Kinases Using Fragment-Led de Novo Design

Structure-based drug design (SBDD) has become a powerful tool utilized by medicinal chemists to rationally guide the drug discovery process. Herein, we describe the use of SPROUT, a de novo-based program, to identify an indazole-based pharmacophore for the inhibition of fibroblast growth factor receptor (FGFR) kinases, which are validated targets for cancer therapy. Hit identification using SPROUT yielded 6-phenylindole as a small fragment predicted to bind to FGFR1. With the aid of docking models, several modifications to the indole were made to optimize the fragment to an indazole-containing pharmacophore, leading to a library of compounds containing 23 derivatives. Biological evaluation revealed that these indazole-containing fragments inhibited FGFR1-3 in the range of 0.8-90 μM with excellent ligand efficiencies of 0.30-0.48. Some compounds exhibited moderate selectivity toward individual FGFRs, indicating that further optimization using SBDD may lead to potent and selective inhibitors of the FGFR family.

Reevaluation of the 2-nitrobenzyl protecting group for nitrogen containing compounds: An application of flow photochemistry

Photochemistry under continuous flow conditions has many potential benefits for photochemical reactions that are problematic in batch. The 2-nitrobenzyl moiety is a photolabile protecting group for nitrogen. However, N-deprotection is generally impractical and, therefore, has not been extensively adopted. This Letter reports significant improvements in the N-deprotection of the 2-nitrobenzyl group through the application of continuous flow photolysis. This procedure was applied to a variety of substrates including indoles, indazoles, pyrazoles and secondary amines. Significant improvement in yield, reaction time and scalability was observed under continuous flow conditions.

Scope of the suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates

A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.

A versatile method for suzuki cross-coupling reactions of nitrogen heterocycles

(Chemical Equation Presented) A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme; dba = dibenzylideneacetone, Cy = cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2-and OH-substituted substrates), and efficient even with unactivated aryl chlorides.

3-(2-(3-Pyridinyl)thiazolidin-4-oyl)indoles, a Novel Series of Platelet Activating Factor Antagonists

(2RS,4R)-3-(2-(3-pyridinyl)thiazolidin-4-oyl)indoles represent a new class of potent, orally active antagonists of platelet activating factor (PAF). The compounds were prepared by acylation of the magnesium or zinc salts of substituted indoles with (2RS,4R)-2-(3-pyridinyl)-3-(tert-butoxycarbonyl)thiazolidin-4-oyl chloride. The 3-acylindole moiety functions as a hydrolytically stabilized and conformationally restricted anilide replacement, which imparts a considerable boost in potency to the series. Structure-activity relationships observed for substitution on the indole ring system are discussed. Members of the series compare favorably with other reported PAF antagonists.