427900-17-2

Usage

Uses

Used in Pharmaceutical Industry:
6-BROMO-N-(PHENYLMETHYL)-2-PYRIDINAMINE is used as an intermediate in the synthesis of various biologically active molecules for the development of new drugs. Its unique structure and reactivity contribute to the creation of innovative pharmaceutical compounds with potential therapeutic applications.
Used in Organic Synthesis:
6-BROMO-N-(PHENYLMETHYL)-2-PYRIDINAMINE serves as a versatile building block in organic synthesis, enabling the development of important chemical compounds with diverse applications. Its presence in the synthesis process can enhance the properties and reactivity of the resulting compounds, broadening the scope of chemical research and innovation.

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 100-46-9 benzylamine 
• 19798-81-3 2-Amino-6-bromopyridine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1589588-48-6 C₆₉H₅₇N₁₅ 
• 1589588-19-1 C₂₃H₂₀BrN₅ 
• 1589587-97-2 C₁₆H₁₂BrClN₄ 
• 427900-22-9 N-(6'-bromo-2'-pyridyl)-N'-(6''-benzylamino-2''-pyridyl)-2,6-diaminopyridine 

Relevant academic research and scientific papers

Rational Optimization of Lewis-Acid Catalysts for Direct Alcohol Amination, Part 2 – Titanium Triflimide as New Active Catalyst

The reactivity of a new titanium triflimide salt (see Part 1) was investigated for the direct amination of alcohols. The combination of this new Lewis acid with pyridine-based ligands allowed a significant increase of activity. The scope of the reaction was increased compared to other Lewis-acid-based protocols. Finally, mechanistic insights based on EPR spectroscopy and DFT calculations are provided.

Discovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases

While several therapeutic options exist, the need for more effective, safe, and convenient treatment for a variety of autoimmune diseases persists. Targeting the Janus tyrosine kinases (JAKs), which play essential roles in cell signaling responses and can contribute to aberrant immune function associated with disease, has emerged as a novel and attractive approach for the development of new autoimmune disease therapies. We screened our compound library against JAK3, a key signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (Ki) as well as on the basis of cellular potency. Optimization of this chemical series led to the identification of VX-509 (decernotinib), a novel, potent, and selective JAK3 inhibitor, which demonstrates good efficacy in vivo in the rat host versus graft model (HvG). On the basis of these findings, it appears that VX-509 offers potential for the treatment of a variety of autoimmune diseases.

Synthesis, structure, and fullerene-complexing property of azacalix[6]aromatics

Synthesis, structure, and fullerene-binding property of azacalix[6]aromatics were systematically studied. By means of [3 + 3] and [2 + 2 + 2] fragment coupling protocols, a number of azacalix[6]aromatics containing different combinations of benzene, pyridine, and pyrimidine rings and various substituents on the bridging nitrogen atoms were synthesized conveniently in moderate to good yields. The resulting macrocycles adopt in the solid state symmetric and heavily distorted 1,3,5-alternate conformations depending on the aromatic building units, whereas, in solution, they exist as a mixture of conformers that undergo rapid interchanges relative to the NMR time scale. All macrocycles were able to form 1:1 complexes with C60 and C 70 in toluene with the association constants up to 7.28 × 104 M-1. In the crystalline state, azacalix[6]aromatics form complexes with C60 and C70 with 2:1, 1:1, and 1:2 stoichiometric ratios between host and guest. Azacalix[6]aromatics interact with fullerene by forming mainly the sandwich structure in which C60 or C70 is sandwiched by two macrocycles. X-ray molecular structures revealed that multiple π-π and CH-π interactions between concave azacalix[6]aromatics and convex fullerenes C60 and C70 contribute a joint driving force to the formation of host-guest complexes.

Iron/amino acid catalyzed direct N-alkylation of amines with alcohols

(Chemical Equation Presented) Ironing it out: The straightforward N-alkylation using alcohols and iron/amino acid catalysis is described (see scheme). The reaction does not proceed by the conventional "borrowing hydrogen" mechanism, but appears to involve a substitution pathway (S N) at the sp3 carbon atom bearing the hydroxy group of the alcohol. Developing a catalyst that is effective at a near neutral pH was key to the successful N-alkylation.

Self-complementarity of oligo-2-aminopyridines: A new class of hydrogen-bonded ladders

A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-α-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization. Although increasing the number of hydrogen-bonding interactions would enhance the hydrogen-bonding stabilization enthalpy, this stabilization enthalpy per unit would be partially sacrificed to compensate for the entropy loss due to dimerization. These results clearly support the importance of preorganization in designing hydrogen-bonding guest - host molecules.

Palladium-catalysed amination of halopyridines on a KF-alumina surface

Palladium-catalysed C-N hetero cross-coupling reactions between bromopyridines and amines (both primary and secondary) can be efficiently performed on a KF-alumina (basic) surface, thus negating the use of strong bases such as sodium tert-butoxide. The reaction conditions are optimised with reference to catalytic systems, solvents and the surface.