142670-87-9

Basic information

• Product Name: N-benzyl-N-(2-chloro-3-pyridinyl) amine
• Synonyms: N-benzyl-N-(2-chloro-3-pyridinyl) amine;N-benzyl-2-chloropyridin-3-amine;Benzyl-(2-chloro-pyridin-3-yl)-amine
• CAS NO: 142670-87-9
• Molecular Formula: C₁₂H₁₁ClN₂
• Molecular Weight: 219
• Mol File: 142670-87-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-benzyl-N-(2-chloro-3-pyridinyl) amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-N-(2-chloro-3-pyridinyl) amine(142670-87-9)
• EPA Substance Registry System: N-benzyl-N-(2-chloro-3-pyridinyl) amine(142670-87-9)

Safety Data

• Hazardous Substances Data: 142670-87-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 830324-68-0 3-(2-chloro-3-pyridyl)-3,4-dihydro-4-oxo-2-quinazolinecarboxylic acid ethyl ester 
• 78607-36-0 2-chloro-3-iodopyridine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 100-52-7 benzaldehyde 
• 956-30-9 2-amino-N-(2-chloropyridin-3-yl)benzamide 
• 386275-19-0 benzylidene(2-chloropyridin-3-yl)amine 
• 100-51-6 benzyl alcohol 
• 52200-48-3 3-bromo-2-chloropyridine 
• 830324-69-1 3,4-dihydro-4-oxo-3-(2-chloro-3-pyridyl)-2-quinazolinecarbothioic acid S-p-tolyl ester 
• 830324-66-8 N-[2-(2-chloro-3-pyridyl)carbamoylphenyl]oxalamic acid ethyl ester 
• 830324-76-0 N-benzyl-3-(2-chloro-3-pyridyl)-3,4-dihydro-4-oxo-2-quinazolinecarboxamide 

Downstream Products

• 105942-43-6 1-(Phenylmethyl)-1H-imidazo<4,5-b>pyridine 

Relevant articles and documents

Study of a new rate increasing "base effect" in the palladium-catalyzed amination of aryl iodides

Evidence for an interphase deprotonation of Pd(II)-amine complexes with weak carbonate base has been gained for the first time. When a rate-limiting deprotonation step is involved in the catalytic cycle, controlling the structure (shape and size of the particles) and/or molar excess of the carbonate base used can significantly increase the reaction rate of Buchwald-Hartwig aminations. By taking such a "base effect" into account a general protocol for the intermolecular amination of aryl iodides with all types of amines has been developed based on a standard Pd-BINAP catalyst, using cesium carbonate as the base.

Streamlined Synthesis of Diaminopyridines by Pd-Catalyzed Ammonia Coupling with Deactivated Amino-Chloropyridines

An efficient and cost-effective two-step synthesis of diaminopyridines, fundamental building blocks of biologically active compounds, is reported. The advantages over previously reported routes include cost and wider availability of the bromo-chloropyridine starting materials and the straightforward accessibility to an extended array of diaminopyridine regioisomers. The key enabler of this synthetic strategy is the development of an unprecedented palladium-catalyzed coupling reaction of ammonia with chloropyridines deactivated by the presence of an alkylamino substituent. The coupling reaction was accomplished with very low catalyst loadings under remarkably mild reaction conditions, making the system particularly suitable for both academic and industrial applications. The utility of this methodology is exemplified by the application to the synthesis of highly relevant scaffolds, including the synthetic intermediates of the marketed drugs Ribociclib and Palbociclib.

Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway

Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).

Asymmetric Hydrogenation of 3-Amido-2-arylpyridinium Salts by Triply Chloride-Bridged Dinuclear Iridium Complexes Bearing Enantiopure Diphosphine Ligands: Synthesis of Neurokinin-1 Receptor Antagonist Derivatives

We describe a most straightforward synthetic method for preparing neurokinin-1 (NK1) receptor antagonist derivatives by asymmetric hydrogenation of 3-amido-2-arylpyridinium salts using dinuclear iridium complexes with enantiopure diphosphine ligands, affo

Synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation of 2-chloro-3-amino-heterocycles

A facile synthesis of imidazo[4,5-b]pyridines and-pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. A model system relevant to the natural product pentosidi

Efficient access to azaindoles and indoles

An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described. Conditions were developed for effective reductive alkylation of electron-deficient o-chlo

Efficient access to cyclic ureas via Pd-catalyzed cyclization

An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines

The general synthesis and a novel intramolecular nucleophilic aromatic substitution (SNAr) reaction of 2-carboxamido-3-arylquinazolin-4- ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utili

Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines

A novel intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-one derivatives induced by base treatment and its application to the expeditious synthesis of secondary aryl amines, including diaryl amines, are descri

SYNTHESE DE N-ALKYL-3-ARYL-2-DIPHENYLPHOSPHINOYL-1H-PYRIDOTHIAZINES

A variete of N-alkyl-3-aryl-2-diphenylphosphinoyl-1H-pyridothiazines has been efficiently synthesized by treatment of the anion of 3-(N-alkyl-N-diphenylphosphinoylmethylamino)-2-chloro or -2,6-dichloropyridines with the appropriate aromatic O-