128562-25-4

Basic information

• Product Name: 4-Pyrrolidin-2-ylpyridine
• Synonyms: 4-PYRROLIDIN-2-YLPYRIDINE;4-(2-PYRROLIDINYL)PYRIDINE;2-(4-PYRIDYL)PYRROLIDINE;4-(2-Pyridyl)pyrrolidine;2-(Pyridin-4-yl)pyrrolidine;2-(4-Pyridinyl)pyrrolidine;Pyridine, 4-(2-pyrrolidinyl)-;4-(pyrrolidin-2-yl)pyridine dihydrochloride
• CAS NO: 128562-25-4
• Molecular Formula: C9H12N2
• Molecular Weight: 148.2
• Product Categories: PYRIDINE;Benzenes;Aromatics;Heterocycles;Heterocycle-Pyridine series
• Mol File: 128562-25-4.mol

Chemical Properties

• Boiling Point: 253.81 °C at 760 mmHg
• Flash Point: 107.301 °C
• Appearance: /
• Density: 1.043 g/cm³
• Vapor Pressure: 0.0179mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.84±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Pyrrolidin-2-ylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyrrolidin-2-ylpyridine(128562-25-4)
• EPA Substance Registry System: 4-Pyrrolidin-2-ylpyridine(128562-25-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 128562-25-4(Hazardous Substances Data)

Usage

Uses

Used in Aldol Catalysis:
4-Pyrrolidin-2-ylpyridine is used as a catalyst in aldol reactions, a fundamental carbon-carbon bond-forming reaction in organic chemistry. Its ability to facilitate the addition of a nucleophile to an aldehyde or ketone makes it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
4-Pyrrolidin-2-ylpyridine is used in the preparation of azole compounds, specifically as 11β-HSD1 inhibitors. These inhibitors play a crucial role in the treatment of metabolic disorders and have potential applications in the development of drugs for diabetes and obesity management.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, 4-Pyrrolidin-2-ylpyridine is utilized for the synthesis of pyrazolodihydropyrimidinylpyrrolidin amide derivatives. These complex organic molecules have potential applications in medicinal chemistry, particularly for the development of novel therapeutic agents with improved selectivity and potency.

InChI:InChI=1/C9H12N2/c1-2-9(11-5-1)8-3-6-10-7-4-8/h3-4,6-7,9,11H,1-2,5H2/p+1/t9-/m1/s1

Upstream product

• 66269-78-1 4-(3,4-dihydro-2H-pyrrol-5-yl)pyridine 
• 1570-45-2 isonicotinic acid ethylester 

Downstream Products

• 343244-28-0 1-[[7-(3,4-Dichloro-phenyl)-4,7-dihydro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]carbonyl]-2-(4-pyridinyl)pyrrolidine 

Relevant articles and documents

Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers

Design and synthesis of pyrazolodihydropyrimidines as KV1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development.

Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles

This paper describes the development of a new catalytic transformation, the ruthenium-catalyzed decarbonylative arylation of cyclic 2-amino esters, which replaces the ester group with an aryl ring at the sp3 carbon center. For example, proline ester amidine 1 is converted to 2-arylpyrrolidine 3 in the presence of arylboronic acids or esters as arene donors and Ru 3(CO)12 as the catalyst. This process provides a rapid access to a variety of 2-arylpyrrolidines and piperidines from commercially available proline, hydroxyproline, and pipecolinate esters. The examination of the substrate scope also showed that many arene boronic acids and boronate esters serve as coupling partners. The high chemoselectivity of this process was demonstrated and ascribed to the significant rate difference between the decarbonylative arylation and the C-H arylation. The decarbonylative arylation complements the C-H arylation, since the latter process lacks control over the extent of functionalization, affording a mixture of mono- and bis-arylpyrrolidines. When applied in tandem, these two processes provide 2,5-diarylpyrrolidines in two steps from the corresponding proline esters. It was also demonstrated that the required amidine or iminocarbamate directing group fulfills two major functions: first, it is essential for the ester activation step, which occurs via the coordination-assisted metal insertion into the acyl C-O bond; second, it facilitates the decarbonylation, via the stabilization of a metallacycle intermediate, assuring the formation of the 2-arylated products instead of the corresponding ketones observed before by others.

Aqueous aldol catalysis by a nicotine metabolite

Nornicotine, an endogenous tobacco alkaloid and minor nicotine metabolite, can catalyze aldol reactions at physiological pH. Catalysis appears to be due to a covalent enamine mechanism, an unprecedented reaction with small organic molecule catalysts in aqueous buffer. Kinetic parameters for nornicotine as well as other related alkaloids were measured and demonstrate that both the pyrrolidine and pyridine rings are critical for optimal catalysis. Substrate compatibility of this catalyst and its implications in vivo are discussed. Copyright