1327885-88-0

Basic information

• Product Name: 3-(4-fluorophenyl)-N-(quinolin-8-yl)butanamide
• Synonyms: 3-(4-fluorophenyl)-N-(quinolin-8-yl)butanamide
• CAS NO: 1327885-88-0
• Molecular Weight: 308.355
• Mol File: 1327885-88-0.mol

Chemical Properties

• CAS DataBase Reference: 3-(4-fluorophenyl)-N-(quinolin-8-yl)butanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-N-(quinolin-8-yl)butanamide(1327885-88-0)
• EPA Substance Registry System: 3-(4-fluorophenyl)-N-(quinolin-8-yl)butanamide(1327885-88-0)

Safety Data

• Hazardous Substances Data: 1327885-88-0(Hazardous Substances Data)

Upstream product

• 732306-64-8 bis(4-fluorophenyl)iodonium triflate 
• 33757-47-0 N-(quinolin-8-yl)butyramide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 16308-15-9 (4-fluorophenyl)-λ³-iodanediyl diacetate 
• 578-66-5 8-amino quinoline 
• 352-34-1 4-fluoro-1-iodobenzene 
• 141-75-3 butyryl chloride 

Relevant articles and documents

Palladium-Catalyzed Base-Promoted Arylation of Unactivated C(sp3)–H Bonds by Aryl Iodides: A Practical Approach To Synthesize β-Aryl Carboxylic Acid Derivatives

A highly efficient protocol for the β-arylation of carboxylic amides by aryl iodides under PdCl2(CH3CN)2/CsOAc catalysis was developed. This method was found to tolerate a broad scope of substrates and was successfully employed in the preparation of a variety of β-aryl α-amino and γ-amino acid derivatives. The utility of this method was further illustrated in the synthesis of the psychotropic drug (±)-phenibut and β-aryl bile acid analogues.

Multicomponent reaction comprising one-pot installation of bidentate directing group and Pd(II)-catalyzed direct β-arylation of C(sp3)[sbnd]H bond of aliphatic and alicyclic carboxamides

In this paper, we report a step-economical one-pot multicomponent reaction protocol comprising the installation of the bidentate directing group (auxiliary) followed by Pd(II)-catalyzed sp3C[sbnd]H activation and β-arylation of various aliphatic/alicyclic carboxamides. Accordingly, the reaction of a mixture of an aliphatic/alicyclic acid chloride, bidentate directing auxiliary (e.g., 8-aminoquinoline) and an aryl iodide in the presence of the Pd(OAc)2catalyst and Ag2CO3additive directly afforded the corresponding β-C[sbnd]H-arylated N-(quinolin-8-yl)carboxamide derivative. To demonstrate the efficiency of the process, various bidentate directing auxiliaries were used and 8-Aminoquinoline was found to be the best directing group for accomplishing the one-pot Pd(II)-catalyzed, sp3C[sbnd]H activation and β-arylation of aliphatic/alicyclic carboxamides. A variety of aliphatic/alicyclic acid chlorides and aryl iodides were used as the substrates and several β-C[sbnd]H arylated carboxamide derivatives were synthesized in moderate to high yields via the multicomponent reaction strategy.

Palladium-catalyzed Cs2CO3-promoted arylation of unactivated C(sp3)-H bonds by (diacetoxyiodo)arenes: Shifting the reactivity of (diacetoxyiodo)arenes from acetoxylation to arylation

PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp3)-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp3)-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.

Pd(II)-catalyzed intermolecular arylation of unactivated C(sp 3)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.

Direct arylation of primary and secondary sp3 C-H bonds with diarylhyperiodonium salts via Pd catalysis

Palladium-catalyzed primary and secondary sp3 C-H bond arylation is reported. The method using diarylhyperiodonium salts as arylation reagents shows good functional group tolerance and proceeds under mild reaction conditions. The KIE experiment