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[1-METHYL-1-(PYRIDIN-2-YL)ETHYL]AMINE is an organic compound that serves as a powerful directing group in the hydroxylation of arenes through copper-mediated C-H activation. It is characterized by its ability to be removed through acid-mediated hydrolysis, making it a versatile and efficient auxiliary in chemical synthesis.

52568-28-2

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52568-28-2 Usage

Uses

Used in Chemical Synthesis:
[1-METHYL-1-(PYRIDIN-2-YL)ETHYL]AMINE is used as a directing group for the hydroxylation of arenes in copper-mediated C-H activation reactions. It enhances the selectivity and efficiency of these reactions, allowing for the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
[1-METHYL-1-(PYRIDIN-2-YL)ETHYL]AMINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to be easily removed through acid-mediated hydrolysis makes it an attractive option for the development of new drugs and drug candidates.
Used in Research and Development:
[1-METHYL-1-(PYRIDIN-2-YL)ETHYL]AMINE is used as a research tool in the development of new synthetic methods and strategies for the hydroxylation of arenes. Its unique properties and reactivity make it a valuable asset in the advancement of organic chemistry and related fields.
Used in Industrial Scale Production:
The Shi Auxiliary, which includes [1-METHYL-1-(PYRIDIN-2-YL)ETHYL]AMINE, has been demonstrated to be effective on a gram-scale, making it a promising candidate for large-scale industrial applications in the synthesis of various organic compounds and pharmaceuticals.

Check Digit Verification of cas no

The CAS Registry Mumber 52568-28-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,5,6 and 8 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 52568-28:
(7*5)+(6*2)+(5*5)+(4*6)+(3*8)+(2*2)+(1*8)=132
132 % 10 = 2
So 52568-28-2 is a valid CAS Registry Number.

52568-28-2Relevant academic research and scientific papers

Stereoselective Synthesis of Chiral β-Fluoro α-Amino Acids via Pd(II)-Catalyzed Fluorination of Unactivated Methylene C(sp3)-H Bonds: Scope and Mechanistic Studies

Zhang, Qi,Yin, Xue-Song,Chen, Kai,Zhang, Shuo-Qing,Shi, Bing-Feng

, p. 8219 - 8226 (2015)

The synthesis of fluorinated complex molecules via direct C(sp3)-H fluorination is attractive yet remains challenging. Here we describe the Pd(II)-catalyzed fluorination of unactivated methylene C(sp3)-H bonds by an inner-sphere mech

Nickel-catalyzed ortho-halogenation of unactivated (hetero)aryl C-H bonds with lithium halides using a removable auxiliary

Zhan, Bei-Bei,Liu, Yan-Hua,Hu, Fang,Shi, Bing-Feng

, p. 4934 - 4937 (2016)

The first example of Ni-catalyzed halogenation of (hetero)aryl C-H bonds with lithium halides (LiX, X = Br, I, Cl) using PIP as a removable directing group is reported. This protocol provides an efficient access to ortho-halogenated (hetero)arenes with operational simplicity, good functional group tolerance, and large-scale synthesis.

Copper-Mediated Thiolation of Unactivated Heteroaryl C?H Bonds with Disulfides under Ligand- and Metal-Oxidant-Free Conditions

Li, Ya,Liu, Yue-Jin,Shi, Bing-Feng

, p. 4117 - 4121 (2017)

Various sulfenylated heteroarenes were synthesized by a copper-mediated C?H thiolation, which was assisted by a 2-(pyridin-2-yl)isopropylamine (PIP-amine) directing group. The reaction features a broad substrate scope, good functional group tolerance, ligand- and metal-oxidant-free conditions, exceptional compatibility with aliphatic disulfides, and excellent yields, providing a highly efficient approach to the biologically important sulfenylated heteroarenes. (Figure presented.).

5-FLUORONICOTINAMIDE DERIVATIVES AND USES THEREOF

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Paragraph 00495-00498, (2021/04/10)

Provided herein is a compound of Formula (I), or pharmaceutically acceptable salt thereof, wherein R1, Y, X, and n are defined herein. Also provided herein are compositions comprising a compound of Formula (I) or pharmaceutically acceptable salt thereof, and methods of using a compound of Formula (I) or pharmaceutically acceptable salt thereof, e.g., in the treatment of heart disease.

HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS

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Paragraph 0405-0406, (2020/08/05)

Aminopyrazine compounds as modulators of an adenosine receptor are provided. The compounds may find use as therapeutic agents for the treatment of diseases mediated through a G-protein-coupled receptor signaling pathway and may find particular use in onco

Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents

Donslund, Aske S.,Neumann, Karoline T.,Corneliussen, Nicklas P.,Grove, Ebbe K.,Herbstritt, Domenique,Daasbjerg, Kim,Skrydstrup, Troels

supporting information, p. 9856 - 9860 (2019/07/09)

Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.

Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent

Yang, Qi-Liang,Wang, Xiang-Yang,Wang, Tong-Lin,Yang, Xiang,Liu, Dong,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng

supporting information, p. 2645 - 2649 (2019/04/17)

The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.

Nickel-Catalyzed Sulfonylation of C(sp2)–H Bonds with Sodium Sulfinates

Liu, Shuang-Liang,Li, Xue-Hong,Zhang, Shu-Sheng,Hou, Sheng-Kai,Yang, Guang-Chao,Gong, Jun-Fang,Song, Mao-Ping

supporting information, p. 2241 - 2246 (2017/07/07)

The first nickel-catalyzed ortho-sulfonylation of C(sp2)–H bonds with sodium sulfinates directed by (pyridin-2-yl)isopropylamine (PIP-amine) is described. This strategy exhibits a broad substrate scope and good functional group tolerance with high monosulfonylation selectivity. Besides arenes and heteroarenes, the reaction can also be extended to alkenes, providing diverse diaryl and alkyl aryl sulfones in high yields. Furthermore, a plausible Ni(I)/Ni(III) mechanism is outlined based on our experimental results and related precedents. (Figure presented.).

NITROGEN-CONTAINING SATURATED HETEROCYCLIC COMPOUND

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Paragraph 0344, (2016/08/29)

The present invention provides a compound represented by the following formula (I) or its pharmaceutically acceptable salt: [wherein, R1 represents optionally substituted C1-4 alkyl, n shows integer of 1 to 4, R2 represents optionally substituted C1-4 alkyl or hydrogen atom, R3 represents optionally substituted C1-4 alkyl, R4a, R4b, R4c, and R4d, similarly or differently, represent optionally substituted C6-14 aryl, optionally substituted C1-4 alkyl, or hydrogen atom and the like, A represents optionally substituted C6-14 aryl or optionally substituted 5 to 11 membered heteroaryl].

Dual Role of Acetate in Copper(II) Acetate Catalyzed Dehydrogenation of Chelating Aromatic Secondary Amines: A Kinetic Case Study of Copper-Catalyzed Oxidation Reactions

Sreenath, Kesavapillai,Yuan, Zhao,Macias-Contreras, Miguel,Ramachandran, Vasanth,Clark, Ronald J.,Zhu, Lei

, p. 3728 - 3743 (2016/08/19)

Copper(II) acetate is a frequent empirical choice of the copper source in copper(II)-mediated redox reactions. The effect of the acetate counterion appears crucial but has not been adequately investigated. Herein, we report that copper(II) acetate catalyz

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