10586-52-4

Usage

Uses

Used in Synthetic Chemistry:
2-Phenyl-1H-pyrrolo[2,3-b]pyridine is used as a synthetic reagent for the preparation of arylbenoxazinones, which are a class of compounds with potential applications in various fields, including pharmaceuticals and materials science. The compound's unique structure allows for the creation of diverse chemical entities through its use in synthetic reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Phenyl-1H-pyrrolo[2,3-b]pyridine is utilized as a key intermediate in the synthesis of various drug candidates. Its structural properties make it a valuable building block for the development of novel therapeutic agents, particularly those targeting complex biological pathways.
Used in Materials Science:
The compound's unique structure and reactivity also make it a candidate for use in the development of new materials with specific properties, such as optoelectronic materials or advanced polymers. Its potential applications in materials science are still being explored, but its unique characteristics suggest a promising future in this field.

Upstream product

• 108-99-6 3-Methylpyridine 
• 100-47-0 benzonitrile 
• 23612-46-6 N-(3-methylpyridin-2-yl)benzamide 
• 1006880-55-2 N-(3-phenylethynyl-pyridin-2-yl)butyramide 
• 2369-18-8 2-fluoro-3-methylpyridine 
• 13534-99-1 2-Amino-3-bromopyridine 
• 98-86-2 acetophenone 
• 271-63-6 7-Azaindole 
• 591-50-4 iodobenzene 
• 536-74-3 phenylacetylene 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 910896-40-1 2-phenyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine 
• 348640-02-8 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine 
• 877593-10-7 methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate 

Downstream Products

• 23616-56-0 3-nitroso-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 521984-94-1 1-methyl-2-phenyl-1H-pyrrolo-[2,3-b]pyridine 
• 521985-26-2 1-methoxymethyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1261726-72-0 4-chloro-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-26-5 4-(4-(4-fluorophenyl)-1-(methoxymethyl)-2-(4-[(triisopropylsilyl)oxy]phenyl)-1H-imidazol-5-yl)-1-(methoxymethyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-25-4 4-(4-(4-fluorophenyl)-1-(methoxymethyl)-2-[4-(methylthio)phenyl]-1H-imidazol-5-yl)-1-(methoxymethyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-17-4 4-[4-(4-fluorophenyl)-1-(methoxymethyl)-2-phenyl-1H-imidazol-5-yl]-1-(methoxymethyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-20-9 4-[4-(4-fluorophenyl)-1-(methoxymethyl)-2-(4-methoxyphenyl)-1H-imidazol-5-yl]-1-(methoxymethyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-22-1 4-[4-(4-fluorophenyl)-1-(methoxymethyl)-2-(3,4,5-trimethoxyphenyl)-1H-imidazol-5-yl]-1-(methoxymethyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-21-0 4-[4-(4-fluorophenyl)-2-[4-(methoxymethoxy)phenyl]-1-(methoxymethyl)-1H-imidazol-5-yl]-1-(methoxymethyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-24-3 4-[4-(4-fluorophenyl)-1-methyl-2-(methylsulfonyl)-1H-imidazol-5-yl]-2-phenyl-1H-pyrrolo[2,3-b]pyridine 
• 1439397-16-6 tert-butyl 1-(4-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)cyclobutylcarbamate 
• 1439397-11-1 1-(4-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)cyclobutanamine 
• 945608-15-1 3-iodo-1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine 

Relevant academic research and scientific papers

Efficient synthesis of 2-substituted 7-azaindole derivatives via palladium-catalyzed coupling and C-N cyclization using 18-crown-6

A practical and straightforward preparation of various novel 2-substituted 7-azaindole derivatives from 2-amino-3-iodopyridine by a two-step procedure is described that gives the desired compounds in good overall yields. Georg Thieme Verlag Stuttgart.

Synthesis of a 7-azaindole by chichibabin cyclization: Reversible base-mediated dimerization of 3-picolines

(Chemical Equation Presented) The lithium diisopropylamide (LDA)-mediated condensation of 2-fluoro-3-picoline and benzonitrile to form 2-phenyl-7-azaindole via a Chichibabin cyclization is described. Facile dimerization of the picoline via a 1,4-addition of the incipient benzyllithium to the picoline starting material and fast 1,2-addition of LDA to benzonitrile cause the reaction to be complex. Both adducts are shown to reenter the reaction coordinate to produce the desired 7-azaindole. The solution structures of the key intermediates and the underlying reaction mechanisms are studied by a combination of IR and NMR spectroscopies.

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.

Palladium-catalyzed regioselective C-2 arylation of 7-azaindoles, indoles, and pyrroles with arenes

A palladium-catalyzed regioselective C-2 arylation of 7-azaindoles, indoles, and pyrroles with arenes has been developed. This study unveils that a critical substrate dependent acid concentration is essential for achieving exclusive C-2 selectivity as wel

The mechanism of lithiation and nitrile insertion reactions of β-methylazines: Evidence from the structure of 3-C5H4NCH=C(Ph)N(H)C(Ph)=NLi · PMDETA

A 1:1:1 reaction of 3-methylpyridine, 1, with LDA and PhCN in the presence of PMDETA gives the title complex 6, shown by X-ray crystallography to be the first monomeric iminolithium. The isolation of 6, and of a cyclised product 8 when a 3:10:3 reaction o

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.

Microwave-assisted synthesis of 7-azaindoles via iron-catalyzed cyclization of an o -haloaromatic amine with terminal alkynes

An efficient and practical procedure was developed to prepare 7-azaindole, starting from an o-haloaromatic amine and corresponding terminal alkynes under microwave irradiation and the scope was demonstrated with a number of examples. The valuable features

Method for directly synthesizing indole by using nitrile

The invention discloses a method for directly synthesizing indole by using nitrile. The method is characterized in that a 2-iodotoluene derivative is served as a substrate, anhydrous copper sulfate, potassium tert-butoxide, a cyanophenyl derivative and the 2-iodophene derivative are mixed according to the molar ratio of (0.02-0.1): (2-4): (5-20):1, reaction is carried out for 4-48 hours at 60-105DEG C in a solvent, petroleum ether/dichloromethane/ethyl acetate are mixed according to the volume ratio of (20-5):10:1 so as to be served as an eluent, and separation is carried out by using a silica gel column so as to obtain a target product. The method has the advantages that the operation is simple, the conditions are mild, the yield is high, and the method is a green and novel synthetic method.

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.