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Usage

Uses

Used in Pharmaceutical Development:
N-(2-phenylethyl)pyridin-2-amine is utilized as a lead compound in the development of new drugs targeting central nervous system disorders. Its interaction with neurotransmitter receptors suggests potential neuroprotective or psychoactive properties, making it valuable for creating medications aimed at treating various neurological conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, N-(2-phenylethyl)pyridin-2-amine serves as a key subject of study. Researchers explore its structure-activity relationships and potential modifications to enhance its therapeutic effects, thereby contributing to the advancement of drug discovery and the creation of more effective treatments for neurological disorders.

Upstream product

• 40825-17-0 Natrium-Verbindung des [2]Pyridylamins 
• 103-63-9 1-phenyl-2-bromoethane 
• 142-08-5 2-Pyridone 
• 64-04-0 phenethylamine 
• 504-29-0 2-aminopyridine 
• 60-12-8 2-phenylethanol 
• 34420-17-2 (2-phenylethyl)boronic acid 
• 100-42-5 styrene 
• 372-48-5 2-fluoropyridine 
• 109-09-1 2-chloropyridine 
• 109-04-6 2-bromo-pyridine 
• 5029-67-4 2-iodopyridine 
• 111098-20-5 N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)pyridin-2-amine 
• 6921-34-2 benzylmagnesium chloride 

Relevant academic research and scientific papers

Rhodium(I) N-heterocyclic carbene complexes as catalysts for the anti-markovnikov hydroaminations of styrene

A series of new rhodium(I) complexes with benzimidazole based N-heterocyclic carbene (NHC) ligand were synthesized by reactions of benzimidazolium salts with [Rh(OMe)COD]2. The characterization of rhodium(I) complexes with the general formula [RhCl(NHC)(4-1,5-cyclooctadiene)] was done by physicochemical and spectroscopic methods. All the synthesized complexes were tested as catalysts in the intermolecular hydroamination reactions between styrene with aromatic amines in ionic liquid. All of these complexes tested here are catalytically active for the intermolecular hydroamination of styrene with aromatic amines in ionic liquid. The anti-Markovnikov addition products were obtained selectively by using 1 mol% of the rhodium complex.

Base-Mediated Site-Selective Hydroamination of Alkenes

We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tertbutoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access-arylamines from terminal aliphatic alkenes.

Ruthenium(II) complexes with chelating n-heterocyclic carbenes and a ruthenate(II) complex as catalysts for the anti-Markovnikov hydroaminations of styrene

New ruthenium chelate and ruthenate complexes were synthesized through the reaction of benzimidazolium salts and [RuCl2(p-cymene)]2 in toluene and characterized by elemental analysis, 1H NMR and 13C NMR spectroscopy. These ruthenium complexes were tested as catalysts in the intermolecular hydroamination reactions between styrene with aromatic amines in ionic liquid. All of these complexes tested here showed good catalytic activity in these reactions. The hydroamination reactions regioselectively produced anti-Markovnikov addition products in moderate to good yields by using 1 mol% of the ruthenium complex.

Palladium/benzimidazolium salt catalyst systems and n-heterocyclic carbene-palladium(II)-pyridine (peppsi) complexes for anti-markovnikov hydroaminations of styrene in ionic liquid

Both in situ prepared Pd-NHC and NHC-Pd-PEPPSI complexes were tested as catalysts in the intermolecular hydroamination reactions between styrene with various anilines in ionic liquid. All of the compounds tested here are catalytically active for the intermolecular hydroamination of styrene with aromatic amines. The anti-Markovnikov addition products were obtained selectively by using 1 mol% of the palladium complex.

Anti-Markovnikov hydroaminations of styrene catalyzed by palladium(II) N-heterocyclic carbene complexes under conventional and microwave heating

Six palladium(II) complexes with benzimidazole-based N-heterocyclic carbene ligands were synthesized by transmetallation reactions between silver(I) N-heterocyclic carbene complexes and PdCl2(PhCN)2. The complexes were characterized by physicochemical and spectroscopic methods. The palladium complexes were tested as catalysts for intermolecular hydroamination reactions of styrene with various anilines in ionic liquids under both conventional and microwave heating. All of these complexes proved to be catalytically active in these reactions. The anti-Markovnikov addition products were selectively obtained by using 1?mol% of the palladium complex.

A segmented flow platform for on-demand medicinal chemistry and compound synthesis in oscillating droplets

We report an automated flow chemistry platform that can efficiently perform a wide range of chemistries, including single/multi-phase and single/multi-step, with a reaction volume of just 14 μL. The breadth of compatible chemistries is successfully demonstrated and the desired products are characterized, isolated, and collected online by preparative HPLC/MS/ELSD.

Intermolecular hydroamination of styrene catalyzed by palladium(II) n-heterocyclic carbene complexes in ionic liquid

PdCl2(NHC)2 complexes have been synthesized by the reaction of palladium acetate with a series of benzimidazolium and imidazolinium salts and characterized by elemental analysis, 1H NMR and 13C NMR spectroscopy. These complexes were used as catalysts for the intermolecular hydroamination reactions between styrene with various anilines in ionic liquid at 160 °C and corresponding anti-Markovnikov products were obtained with a selectivity of 100% in good yields.

Selective Monoarylation of Primary Amines Using the Pd-PEPPSI-IPentCl Precatalyst

A single set of reaction conditions for the palladium-catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd-PEPPSI-IPentCl catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and initiation) with the soluble and nonaggressive sodium salt of BHT (BHT=2,6-di-tert-butyl-hydroxytoluene), both six- and five-membered (hetero)aryl halides undergo efficient and selective amination.

A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N -Benzyl-2-aminopyridines via C-C and C-N bond cleavage

A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C-C and C-N bond cleavage.

Cu-catalyzed carbon-heteroatom coupling reactions under mild conditions promoted by resin-bound organic ionic bases

Resin-bound organic ionic bases (RBOIBs) were developed in which tetraalkyl-ammonium or phosphonium cations are covalently attached to solid resins. The application tests showed that the performance of the tetraalkyl-ammonium-type RBOIBs is slightly better than that of the corresponding Cs salts in Cu-catalyzed C-N cross-couplings, while the tetraalkylphosphonium-type RBOIBs are significantly better than all the inorganic bases. With these newly developed RBOIBs, room-temperature Cu-catalyzed C-Ncoupling with various nonactivated aryl iodides and even aryl bromides can be readily accomplished. Moreover, RBOIBs can be easily recycled and reused for a number of times without much drop of activity. The good performances of RBOIBs are proposed to arise from the relatively weak binding forces between the cationic polymer backbone and basic anions, as opposed to the strong metal-anion interactions in the inorganic bases. Further applications of RBOIBs in Ni-catalyzed Suzuki-type couplings at room temperature, Cu-catalyzed C-N couplings at -30 °C, a Pd-catalyzed Heck reaction at 60 °C, and Cu-catalyzed C-S couplings at room temperature demonstrate that RBOIBs are generally applicable bases with improved performance for many other types of organic transformations.