116359-75-2

Basic information

• Product Name: 3-methyl-1-pyridin-2-yl-1H-indole
• Synonyms: 3-methyl-1-pyridin-2-yl-1H-indole
• CAS NO: 116359-75-2
• Molecular Formula: C₁₄H₁₂N₂
• Molecular Weight: 208
• Mol File: 116359-75-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methyl-1-pyridin-2-yl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-pyridin-2-yl-1H-indole(116359-75-2)
• EPA Substance Registry System: 3-methyl-1-pyridin-2-yl-1H-indole(116359-75-2)

Safety Data

• Hazardous Substances Data: 116359-75-2(Hazardous Substances Data)

Usage

Commonly known as

MPI

Class

Indole derivative

Molecular structure

Consists of an indole ring substituted with a methyl group and a pyridine ring

Pharmacological activities

Studied for effects on central nervous system, potential as antineoplastic agent, role in treatment of neurodegenerative diseases, potential as anti-inflammatory and antioxidant agent

Therapeutic potential

Continues to be explored for potential therapeutic applications and mechanisms of action.

Upstream product

• 109-09-1 2-chloropyridine 
• 83-34-1 3-Methylindole 
• 109-04-6 2-bromo-pyridine 
• 5029-67-4 2-iodopyridine 
• 372-48-5 2-fluoropyridine 

Downstream Products

• 1401518-63-5 2-(4-fluorophenyl)-3-methyl-1-(pyridin-2-yl)-1H-indole 
• 1401518-62-4 2-(4-methoxyphenyl)-3-methyl-1-(pyridin-2-yl)-1H-indole 
• 1283073-92-6 3-methyl-2-phenyl-1-(pyridin-2-yl)-1H-indole 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 

Relevant articles and documents

Cp?CoIII-Catalyzed Synthesis of Pyrido[2′,1′:2,3]pyrimido[1,6-a]indol-5-iums via Tandem C-H Activation and Subsequent Annulation from 1-(Pyridin-2-yl)-1H-indoles and Internal Alkynes

A Cp?CoIII-catalyzed C2-selective C-H alkenylation/annulation cascade transformation of 1-(pyridin-2-yl)-1H-indoles with internal alkynes to afford pyrido[2′,1′:2,3]pyrimido[1,6-a]indol-5-iums is presented. Moreover, 6,7-dihydro-4H-pyrido[2′,1′:2,3]pyrimido[1,6-a]indole, a new functionalized N-fused indole core heterocycle, could be constructed effectively via reduction of pyrido[2′,1′:2,3]pyrimido[1,6-a]indol-5-ium by NaBH4.

N-substituted aminobiphenyl palladacycles stabilized by dialkylterphenyl phosphanes: Preparation and applications in C[sbnd]N cross-coupling reactions

Neutral and cationic N-methyl- and N-phenyl-2-aminobiphenyl methanesulfonate palladacycles stabilized with dialkylterphenyl phosphanes have been prepared and characterized. Neutral structures are favored with the less bulky phosphane PMe2ArXyl2, L1, while more sterically demanding ligands PiPr2ArXyl2, L3, and PCyp2ArXyl2 (Cyp = cyclopentyl), L4, lead to cationic complexes in which the phosphane exhibits a bidentate κ1-P, η1-Carene coordination mode involving one of the ipso carbon atoms of a flanking terphenyl aryl ring. The complexes were evaluated for activity in C[sbnd]N cross-coupling reactions and [Pd(N-methyl-2-aminobiphenyl)L4](OMs) (OMs = mesylate) was identified as the most efficient precatalyst, facilitating the coupling of aryl chlorides with secondary and primary amines and indoles.

Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: Facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols

An unusual Rh/Cu-catalyzed synthesis of pyrido[2,1-a]indoles starting from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols was presented. The multi-step cascade transformations formally involve the cleavage of two C-H, three C-C, and one C-N bonds with concomitant construction of two C-H, four C-C, and one C-N bonds with excellent chemoselectivity in one-pot reaction.

Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

An asymmetric hydroarylative cyclization of enynes involving a C-H bond cleavage is reported. The cobalt-catalyzed cascade generates three new bonds in an atom-economical fashion. The products were obtained in excellent yields and excellent enantioselectivities as single diastereo- and regioisomers. Preliminary mechanistic studies indicate that the reaction shows no intermolecular C-H crossover. This work highlights the potential of cobalt catalysis in C-H bond functionalization and enantioselective domino reactivity.

Nitroarenes as the Nitrogen Source in Intermolecular Palladium-Catalyzed Aryl C–H Bond Aminocarbonylation Reactions

A three-component palladium-catalyzed aminocarbonylation of aryl and heteroaryl sp2 C?H bonds using nitroarenes as the nitrogen source was achieved using Mo(CO)6 as the reductant and origin of the CO. This intermolecular C?H bond functionalization does not requires any exogenous ligand to be added, and our mechanism experiments indicate that the palladacycle catalyst serves two roles in the aminocarbonylation reaction: reduce the nitroarene to a nitrosoarene and activate the sp2 C?H bond.

Palladium-catalysed direct C-2 methylation of indoles

A direct C-2 methylation reaction of indoles bearing a readily removable N-2-pyrimidyl moiety as a site-specific directing group has been developed with a palladium catalyst. This reaction relied on the use of KF to promote efficient methylation. A moderate to good yield was achieved in a range of indole substrates.

C-N coupling of indoles and carbazoles with aromatic chlorides catalyzed by a single-component NHC-nickel(0) precursor

A new and efficient nickel-based protocol for the N-arylation of indoles and carbazoles with aromatic chlorides, the least expensive of the aryl halides, is described. The procedure provides selectively N-(hetero)arylation products in good to high yields, in short reaction times and without adding an excess of ligands.

Ruthenium-catalyzed heteroatom-directed regioselective C-H arylation of indoles using a removable tether

A new approach to C-2 arylated indoles has been developed by utilizing a ruthenium-catalyzed, heteroatom-directed regioselective C-H arylation. The reaction is highly site-selective and results in very good yields. The highlight of the work is the use of a removable directing group and compatibility of the catalytic system with halogen functional groups in the substrates.

Benzotriazol-1-ylmethanol: An excellent bidentate ligand for the copper/palladium-catalyzed C-N and C-C coupling reaction

An efficient benzotriazole based N,O bidentate ligands for the Cu-catalyzed N-arylation of π-excessive nitrogen heterocycles is described. This ligand accomplishes C-N coupling of Nheterocycles and C-C coupling of boronic acids with a variety of hindered, functionalized aryl/heteroaryl halides under mild reaction conditions in good to excellent yields. Using his ligand C-N and C-C (Suzuki) couplings with bromoarenes could be conducted with less catalyst loading. A wide array of deactivated and hindered aryl halides react cleanly to afford the functionalized biaryl derivatives in high yields. ARKAT-USA, Inc.

Palladium-assisted regioselective C-H cyanation of heteroarenes using isonitrile as cyanide source

A palladium-catalyzed regioselective C-H cyanation of heteroarenes was achieved using tert-butyl isocyanide as "CN" source, which provides a new and unique strategy for the preparation of (hetero)aryl nitriles. Indoles, pyrroles, and aromatic rings could be efficiently cyanated through C-H bond activation with high regioselectivity.