85895-80-3

Usage

Uses

Used in Pharmaceutical Research:
6-methyl-N-(6-methyl-2-pyridyl)pyridin-2-amine is used as a building block for the synthesis of biologically active compounds, contributing to the development of new pharmaceutical agents.
Used in Medicinal Chemistry:
Due to its structural properties and reactivity, 6-methyl-N-(6-methyl-2-pyridyl)pyridin-2-amine is utilized in medicinal chemistry for the design and synthesis of novel drug candidates.
Used in Drug Development:
This chemical compound may have potential applications in drug development, where its unique structure can be leveraged to create new therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C12H13N3/c1-9-5-3-7-11(13-9)15-12-8-4-6-10(2)14-12/h3-8H,1-2H3,(H,13,14,15)

Upstream product

• 1824-81-3 2-Amino-6-methylpyridine 
• 18368-63-3 6-chloro-2-picoline 
• 5315-25-3 2-bromo-6-methylpyridine 

Relevant academic research and scientific papers

Nickel-Catalyzed C-N Cross-Coupling of Ammonia, (Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides Enabled by Ligand Design

The Ni(II) precatalyst (C1) featuring the phosphonite ancillary ligand Phen-DalPhos (L1) was employed in the cross-coupling of (hetero)anilines with (hetero)aryl chlorides and in the diarylation of ammonia with (hetero)aryl chlorides to afford heteroatom-dense di(hetero)arylamines. The PAd2-DalPhos precatalyst C4 provided complementary reactivity in cross-couplings of indoles with (hetero)aryl chlorides. Taken together, the demonstration of room-temperature reactivity within each of the reaction classes examined and the observation of useful chemoselectivity at low loading (≤0.5 mol % Ni) and on gram-scale distinguishes C1 and C4 from other metal catalysts (i.e., copper, palladium, nickel, or other) within the field of C-N cross-coupling chemistry.

NHC copper(I) complexes bearing dipyridylamine ligands: Synthesis, structural, and photoluminescent studies

We describe the synthesis of new cationic tricoordinated copper complexes bearing bidentate pyridine-type ligands and N-heterocyclic carbene as ancillary ligands. These cationic copper complexes were fully characterized by NMR, electrochemistry, X-ray analysis, and photophysical studies in different environments. Density functional theory calculations were also undertaken to rationalize the assignment of the electronic structure and the photophysical properties. These tricoordinated cationic copper complexes possess a stabilizing CH-π interaction leading to high stability in both solid and liquid states. In addition, these copper complexes, bearing dipyridylamine ligands having a central nitrogen atom as potential anchoring point, exhibit very interesting luminescent properties that render them potential candidates for organic light-emitting diode applications.

The synthesis and application of novel Ni(ii) N-alkyl dipyridylaldiminato complexes as selective ethylene oligomerisation catalysts

A series of N-alkyl 2,2′-dipyridylamine ligands of general formula (2-C5H3NR)2NR′, (a): R = H, R′ = Me; (b): R = H, R′ = benzyl; (c): R = H, R′ = methylcyclohexyl; (d): R = H, R′ = neopentyl; (e): R = Me, R′ = Me) were prepared by a modified method involving base-mediated N-alkylation with the respective alkyl halide. Reaction of the ligands, a-e, with NiCl2(DME) allowed for the isolation of μ-Cl Ni(ii) complexes: [Ni(μ-Cl){a}Cl]2 (1a); [Ni(μ-Cl){b}Cl]2 (1b); [Ni(μ-Cl){c}Cl]2 (1c); [Ni(μ-Cl){d}Cl]2 (1d) and [Ni(μ-Cl){e}Cl]2 (1e). The complexes were characterised by FT-IR spectroscopy, magnetic susceptibility measurements, mass spectrometry, elemental analyses and in the case of 1a, SCD analysis. In the case of complex 1e, an acid-mediated hydrolysis process was identified. The product of hydrolysis, the protonated ligand and a tetrachloronickelate salt (1e-A), was characterised by SCD analysis. Activation of 1a-1e with alkyl aluminium reagents generated highly active catalysts for the oligomerisation of ethylene, with activities of up to 864 kg oligomers molNi-1 h-1 and high selectivity toward the formation of butenes. In general, trans 2-butene was observed as the major isomer, with the exception of 1e. In the case of 1e, the selectivity for 1-butene was 98%, thereby demonstrating the significant effect that the introduction of a low degree of steric pressure in the coordination sphere of the catalyst has on selectivity.

Reactivity of bis(pyridyl)- N -alkylaminato methylpalladium complexes toward ethylene: insights from experiment and theory

A series of novel neutral and cationic methylpalladium complexes bearing N-alkyl-2,2-dipyridylaldiminato ligands were prepared and characterized. In the presence of ethylene, the cationic complexes were active as dimerization catalysts, producing a mixture of 1- and 2-butenes. A Pd-ethyl π-ethylene species was identified as the catalyst resting state by low-temperature spectroscopic and DFT studies, which provided insights into the effect of both steric and electronic factors on the observed reactivity.

Selective one-pot synthesis of symmetrical and unsymmetrical di- and triarylamines with a ligandless copper catalytic system

The one-pot synthesis of symmetrical or unsymmetrical di- or triarylamines using aryl iodides or bromides and LiNH2 as ammonia source is reported. This highly selective method is based, for the first time, on a copper-catalyzed system, which does not require the presence of any additional ligand.

Towards selective ethylene tetramerization

And the magic number is... . A large amount of oligomer-free 1-octene (99.9%) was produced from ethylene by a catalytic system based on chromium during the formation of polyethylene wax [see GC-MS chromatogram; the other three significant peaks are methanol (quenching agent), ethyl acetate (needle-rinsing agent), and toluene (solvent)]. Copyright

Highly efficient and economic synthesis of new substituted amino-bispyridyl derivatives via copper and palladium catalysis

A convenient route for the synthesis of a variety of amino-bispyridyl compounds is introduced. Bispyridylamines were prepared in three steps from commercially available 2,6-dibromopyridine, via a copper mediated alkylation followed by two consecutive N-arylation reactions catalyzed by copper and palladium, respectively.

N-Acyl-N,N-dipyridyl and N-acyl-N-pyridyl-N-quinoyl amine based palladium complexes. Synthesis, X-ray structures, heterogenization and use in Heck couplings

A series of homogeneous and heterogeneous palladium(II)-catalysts and their use in Heck-couplings is described. Starting from four different amines, N-pyrid-2-yl-N-(3-methylpyrid-2-yl)amine (1), N-pyrid-2-yl-N-(6-methylpyrid-2-yl)amine (2), N-(6-methylpyrid-2-yl)-N-(4-methylquinolin-2-yl)amine (3) and N-bis(6-methylpyrid-2-yl)amine (4), the corresponding acetyl- and norbornene derivatives, N-pyrid-2-yl-N-(3-methylpyrid-2-yl) acetamide (5), N-pyrid-2-yl-N-(6-methylpyrid-2-yl) acetamide (6), N-(6-methylpyrid-2-yl)-N-(4-methylquinolin-2-yl) acetamide (7), N-bis(6-methylpyrid-2-yl)acetamide (8) and N-pyrid-2-yl-N-(3-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide (9), N-pyrid-2-yl-N-(6-methylpyrid-2-yl)-endo-norborn-2-ene-5-carbamide (10) and N-(6-methylpyrid-2-yl)-N-(4-methylquinolin-2-yl)-endo-norborn-2-ene-5-carbamide (11), respectively, have been prepared. The acetyl derivatives 5-8 have been used for the preparation of the homogeneous Heck catalysts N-acetyl-N-pyrid-2-yl-N-(3-methylpyrid-2-yl)amine palladium dichloride (13), N-acetyl-N-pyrid-2-yl-N-(6-methylpyrid-2-yl)amine palladium dichloride (14), N-acetyl-N-(6-methylpyrid-2-yl)-N-(4-methylquinolin-2-yl)amine palladium dichloride (15) and N-acetyl-N-bis(6-methylpyrid-2-yl)amine palladium dichloride (16). X-ray data were obtained for compounds 9, 11, 13 and 14. Polymer supports 17-19 were prepared via ring-opening metathesis copolymerization of the norbornene derivatives 9-11 with 1,4,4a,5,8,8a-hexahydro-1,4,5,8-exo-endo-dimethano-naphthalene (HDMN-6) and subsequently loaded with palladium(II) chloride. Both the homogeneous catalysts 13-16 and the heterogeneous catalysts are active in the vinylation of aryl iodides and aryl bromides with turn-over numbers (TONs) of up to 220 000. Comparably low yields (=34%) and TONs (=2100) are achieved in the tetrabutylammonium bromide- (TBAB-) assisted vinylation of aryl chlorides as well as in the amination of aryl bromides. Structural data of compounds 9, 11, 13 and 14 were compared with those of the parent systems, N-acetyldipyridylamine palladiumdichloride (20) and the poly(N,N-dipyrid-2-yl-endo-norborn-2-ene-5-carbamide)based resin (21), respectively. Thus, methyl-substitution leads to a significant perturbation of the almost perfect square planar coordination of Pd found in 20 resulting in lowered stabilities of the corresponding Pd-complexes 13-16 and consequently lowered coupling yields compared to 20 and 21.