32631-59-7

Upstream product

• 5315-25-3 2-bromo-6-methylpyridine 
• 62-53-3 aniline 
• 63071-03-4 2-methoxy-6-methyl-pyridine 
• 1824-81-3 2-Amino-6-methylpyridine 
• 108-86-1 bromobenzene 

Downstream Products

• 1570075-56-7 N-([1,1'-biphenyl]-2-yl)-6-methylpyridin-2-amine 
• 1570075-60-3 6-methyl-N,N-diphenylpyridin-2-amine 
• 1283074-00-9 C₂₆H₂₀N₂ 

Relevant academic research and scientific papers

Synthesis method of aza-arylamine compound and aza-arylamine compound

The invention provides a synthesis method of an aza-arylamine compound as shown in a formula (I). The synthesis method comprises the following steps: an aza aromatic hydrocarbon compound as shown in aformula (II) reacts with an amine compound as shown in a formula (III) in presence of alkali and under a heating condition, so that u X substituent groups on an A ring of the compound as shown in theformula (II) are substituted by NRR in the compound as shown in the formula (III), and the compound as shown in the formula (I) is obtained, wherein A is an aza six-membered aromatic ring or five-membered aromatic ring, and is an independent single ring or is fused with a ring B; X refers to that the A ring has at least n X substituent groups, each X substituent group is independently selected from the group consisting of F, Cl, Br, I, CN, alkoxy of C and alkylthio of C, and n is a positive integer selected from 1-5; and the alkali is one or a mixture of more selected fromof BuOK, BuONa, BuONa, KHMDS, NaHMDS and LiHMDS. The synthesis method provided by the invention does not need the use of transition metal catalysts, is simple and convenient to operate, is economical and practical and is environmentally friendly. In addition, the invention also provides the aza-arylamine compound prepared by the method.

Anticancer-Active N-Heteroaryl Amines Syntheses: Nucleophilic Amination of N-Heteroaryl Alkyl Ethers with Amines

A mild amination protocol of N-heteroaryl alkyl ethers with various amines is described. This transformation is achieved by utilizing simple and readily available base as promoter via C-O bond cleavage, offering a new amination strategy to access several anticancer-active compounds. This work is highlighted by the excellent functional group compatibility, scalability, wide substrate scope, and easy derivatization of a variety of drugs.

Use of a "catalytic" Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch

A general, efficient method for C-N cross-coupling has been developed using N,N-dimethyloctanamide as a catalytic cosolvent for biphasic continuous-flow applications. The described method was used to generate a variety of biarylamines and was integrated into a two-step sequence which converted phenols into biarylamines via either triflates or tosylates. Additionally, the method was applied to a three-step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches. Going with the flow: A general flow method developed for C-N cross-coupling using N,N-dimethyloctanamide as a catalytic cosolvent was integrated into a two-step sequence which converted phenols into biarylamines via either triflates or tosylates. It was applied to a three-step synthesis of imatinib, the API of Gleevec, in good yield without the need of solvent switches.

Synthesis of polyfunctional secondary amines by the addition of functionalized zinc reagents to nitrosoarenes

Addition of functionalized aryl, heteroaryl or adamantyl zinc reagents to various nitroso-arenes in the presence of magnesium salts and LiCl in THF produces after a reductive work-up with FeCl2 and NaBH4 in ethanol the corresponding polyfunctional secondary amines in high yields. This journal is

Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications

The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.

Ligand free copper-catalyzed N-arylation of heteroarylamines

An efficient protocol for ligand-free Cu-catalyzed N-arylation of heteroarylamines has been developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines to afford the corresponding products in high yields. Further, this protocol is particularly suitable for reactions of the most hindered aryl iodides with 2-aminopyridines.

Palladium-catalyzed oxidative alkynylation of arene C-H bond using the chelation-assisted strategy

Palladium-catalyzed alkynylation of arene C-H bonds with (triisopropylsilyl)acetylene was developed for the first time under oxidative conditions in the present study. Among various type of directing groups examined, the N-phenyl-2-aminopyridine skeleton was shown to be most effective and selective for the Pd-catalyzed direct alkynylation reaction, and the desired alkynylated products were obtained in moderate to good yields.

Rhodium(NHC)-catalyzed amination of aryl bromides

(Figure Presented) A rhodium-catalyzed amination reaction of aryl halides with amines has been developed with the use of a N-heterocyclic carbene (NHC) ligand (I/Pr = 1,3-diisopropylimidazol-2-ylidene). The active metal species responsible for the reaction progress was identified. The developed procedure of the Rh-catalyzedW-arylation is convenient to carry out under mild reaction conditions displaying a wide range of substrate scope and high degree of functional group tolerance.

Identification of G protein-coupled receptor 120-selective agonists derived from PPARγ agonists

A weak, nonselective G protein-coupled receptor 120 (GPR 120) agonist 10 was found by screening a series of carboxylic acids derived from the peroxisome proliferator-activated receptor γ (PPARγ) agonist 3. Modification based on the homology model of GPR12

3-piperidyl-4-oxoquinazoline derivatives and pharmaceutical compositions comprising the same

3-piperidyl-4-oxoquinazoline derivatives are provided, which is represented by the formula (I): wherein R represents an amino group or a cyclic amino group such as dibenzoazepine, each of which is substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the like, n is an integer of 1 to 3, R3and R4independently represents a hydrogen atom, a lower alkyl group, or the like, or a pharmaceutically acceptable salt thereof. Compounds (I) of the present invention have excellent MTP-inhibitory activity. Thus, these compounds not only inhibit formation of LDL that is a cause of arteriosclerotic diseases but also regulate TG, cholesterol, and lipoproteins such as LDL in the blood and regulate cellular lipids through regulation of MTP activity. They can also be used as a new type of preventive or therapeutic agents for hyperlipemia or arteriosclerotic diseases. Furthermore, they can be used as therapeutic or preventive agents for pancreatitis, obesity, hypercholesterolemia, and hypertriglyceridemia.