10299-55-5

Basic information

• Product Name: 3-Phenyl-7-azaindole
• Synonyms: 3-Phenyl-7-azaindole;3-phenyl-1H-Pyrrolo[2,3-b]pyridine
• CAS NO: 10299-55-5
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.2319
• Mol File: 10299-55-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Phenyl-7-azaindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-7-azaindole(10299-55-5)
• EPA Substance Registry System: 3-Phenyl-7-azaindole(10299-55-5)

Safety Data

• Hazardous Substances Data: 10299-55-5(Hazardous Substances Data)

Usage

General Description

3-Phenyl-7-azaindole is a chemical compound with the molecular formula C13H10N2. It is a substituted indole derivative containing a phenyl group at the 3-position. 3-Phenyl-7-azaindole has been studied for its potential biological activities, including as a ligand for the serotonin 5-HT6 receptor and as a building block for the synthesis of pharmaceutical compounds. It has also been investigated for its potential use in the development of organic light-emitting diodes (OLEDs) and other optoelectronic applications. 3-Phenyl-7-azaindole is a versatile compound with potential uses in various fields, and further research on its properties and applications is ongoing.

Upstream product

• 54231-33-3 3-bromo-2-nitropyridine 
• 1311484-52-2 MIDA alkenyl-2-boronate 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 271-63-6 7-Azaindole 
• 98-80-6 phenylboronic acid 
• 100-63-0 phenylhydrazine 
• 226085-18-3 3-bromo-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine 
• 74420-15-8 3-bromo-1H-pyrrolo[2,3-b]pyridine 

Relevant articles and documents

A palladium-catalyzed Barluenga cross-coupling – Reductive cyclization sequence to substituted indoles

A short and flexible synthesis of substituted indoles employing two palladium-catalyzed reactions, a Barluenga cross-coupling of p-tosylhydrazones with 2-nitroarylhalides followed by a palladium–catalyzed, carbon monoxide–mediated reductive cyclization has been developed. A one-pot, two-step methodology was further developed, eliminating isolation and purification of the cross-coupling product. This was accomplished by utilizing the initially added 0.025 equivalents of bis(triphenylphosphine)palladium dichloride, thus serving a dual role in the cross-coupling and the reductive cyclization. It was found that addition of 1,3-bis(diphenylphosphino)propane and carbon monoxide after completion of the Barluenga reaction afforded, in most cases, significantly better overall yields.

Synthesis method of palladium-catalyzed 3-aryl 7-azaindole compound

A synthesis method of a palladium-catalyzed 3-aryl 7-azaindole compound comprises the following steps: adding a 7-azaindole compound and an arylboronic acid compound into a reaction tube, adding a transition metal palladium catalyst, an oxidizing agent, alkali and a solvent, and reacting at 40-100 DEG C for 2-24 hours to obtain the 3-aryl 7-azaindole compound. In the invention, the reaction systemdoes not need additional addition of N-containing and P-containing ligands; the N1-site protective group in the 7-azaindole compound is not important, whether the N1-site protective group exists or not has no obvious influence on the activity and selectivity of the arylation reaction, and the reaction can selectively occur at the C3 site of the 7-azaindole compound; the arylboronic acid compoundis used as an arylation reagent, so that toxicity is obviously reduced, and high-pollution halides cannot be generated in the reaction process; the whole reaction process is simple, efficient, low intoxicity and convenient to operate.

Vinylic MIDA boronates: New building blocks for the synthesis of aza-heterocycles

Abstract A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif. Old dog, new tricks: A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic β-aminophosphonate motif.