38210-35-4

Usage

Uses

Used in Organic Synthesis:
2-(2-Pyridyl)benzothiophene, 97 is used as a key intermediate in organic synthesis for the creation of a broad spectrum of chemical compounds. Its unique structure allows for versatile chemical reactions, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(2-Pyridyl)benzothiophene, 97 is employed as a building block for the development of novel drug candidates. Its incorporation into molecular structures can potentially lead to the discovery of new therapeutic agents with improved pharmacological properties.
Used in Laboratory and Research Applications:
Due to its high purity level, 2-(2-Pyridyl)benzothiophene, 97 is suitable for use in various laboratory and research settings. It serves as a reliable component in experiments and studies aimed at understanding the properties and potential applications of heterocyclic aromatic compounds.

InChI:InChI=1/C13H9NS/c1-2-7-12-10(5-1)9-13(15-12)11-6-3-4-8-14-11/h1-9H

Upstream product

• 109-04-6 2-bromo-pyridine 
• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 95-15-8 Benzo[b]thiophene 
• 878376-35-3 pyridine-2-sulfonyl fluoride 
• 1072-85-1 o-fluorobromobenzene 
• 1945-84-2 2-ethynylpyridine 
• 63724-94-7 2-deuteriobenzothiophene 
• 5029-67-4 2-iodopyridine 
• 109-09-1 2-chloropyridine 
• 33775-94-9 2-(methylthio)iodobenzene 
• 376584-76-8 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene 
• 568572-21-4 2-(benzo[b]thiophen-2-yl)boronic acid neopentyl glycol ester 
• 1209496-06-9 C₁₃H₁₅BO₃S 
• 583-53-9 2,3-dibromobenzene 

Downstream Products

• 1610885-83-0 (4-Fluorophenyl)(2-(pyridin-2-yl)benzo[b]thiophen-3-yl)methanone 
• 1610885-82-9 (4-methoxyphenyl)(2-(pyridin-2-yl)benzo[b]thiophen-3-yl)methanone 
• 1627500-40-6 C₂₂H₁₂F₅NOS 
• 1232366-71-0 C₃₁H₃₀BNS 
• 1610885-81-8 (3,5-dimethylphenyl)(2-(pyridin-2-yl)benzo[b]thiophen-3-yl)methanone 

Relevant academic research and scientific papers

Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts

Herein are reported ligand-coupling reactions of Grignard reagents with pyridylsulfonium salts. The method has wide functional group tolerance and enables the formation of bis-heterocycle linkages, including 2,4′-, 2,3′-, and 2,2′-bipyridines, as well as pyridines linked to pyrimidines, pyrazines, isoxazoles, and benzothiophenes. The methodology was successfully applied to the synthesis of the natural products caerulomycin A and E.

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Trithiocarbonate Anion as a Sulfur Source for the Synthesis of 2,5-Disubstituted Thiophenes and 2-Substituted Benzo[ b]thiophenes

The trithiocarbonate anion (CS32-) was generated in situ from CS2 and KOH in dimethyl sulfoxide by a simple method and used as a novel synthetic equivalent of the S2- synthon for the synthesis of 2,5-disubstituted thiophenes from 1,3-butadiynes. Additionally, this system was employed for the metal-free synthesis of 2-substituted benzo[b]thiophenes from 2-haloalkynyl (hetero)arenes. These compounds were obtained from a cheap and readily available sulfur source in moderate to good yields, with good functional group tolerance.

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.

The synthesis of cyclometalated platinum(ii) complexes with benzoaryl-pyridines as C^N ligands for investigating their photophysical, electrochemical and electroluminescent properties

A series of (C^N)Pt(acac)-type complexes has been successfully synthesized with a benzo[b]furan, benzo[b]thiophene, benzo[b]selenophene, or benzo[b]tellurophene group in the benzoaryl-pyridine ligand. Using X-ray crystallography, the chemical structures o

Palladium/Copper Dual Catalysis for the Cross-Coupling of Aryl(trialkyl)silanes with Aryl Bromides

Whereas aryl(trialkyl)silanes are considered to be ideal organometallic reagents for cross-coupling reactions owing to their stability, low toxicity, solubility, and easy accessibility, they are generally inert under typical cross-coupling conditions. Disclosed herein is a palladium/copper catalytic system that enables the cross-coupling of trimethyl, triethyl, tert-butyldimethyl, and triisopropyl aryl silanes with aryl bromides. This process is applicable to the sequential C?H and C?Si bond arylation of thiophenes and the synthesis of poly(thiophene–fluorene)s.

The Highly Efficient Suzuki–Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by “Bulky-yet-Flexible” Palladium–PEPPSI Complexes in Air

A series of Pd–PEPPSI complexes were designed and synthesized. The relationship between catalyst structure and properties was systematically investigated. It was revealed that “bulky-yet-flexible” C3 bearing ancenaphthyl backbone was a highly efficient precatalyst and could be successfully employed in Suzuki–Miyaura reactions of (hetero)aryl chlorides with (hetero)arylboronic acids at a low palladium loading in the presence of a weak inorganic base in air.

Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation

An efficient and direct ruthenium-catalyzed regioselective hydroxymethylation of (hetero)arenes via C-H activation with paraformaldehyde as a hydroxymethylating reagent is described. The corresponding products can be obtained in good to excellent yield. A number of aryl aldehydes can also be used in place of paraformaldehyde giving the desired alcohol products with similarly good results.

Photosensitization Behavior of Ir(III) Complexes in Selective Reduction of CO2 by Re(I)-Complex-Anchored TiO2 Hybrid Catalyst

A series of cationic Ir(III) complexes ([Ir(btp)2(bpy-X2)]+ (Ir-X+: btp = (2-pyridyl)benzo[b]thiophen-3-yl; bpy-X2 = 4,4′-X2-2,2′-bipyridine (X = OMe, tBu, Me, H, and CN)) were applied as visible-light photosensitizer to the CO2 reduction to CO using a hybrid catalyst (TiO2/ReP) prepared by anchoring of Re(4,4′-Y2-bpy)(CO)3Cl (ReP; Y = CH2PO(OH)2) on TiO2 particles. Irradiation of a solution containing Ir-X+, TiO2/ReP particles, and an electron donor (1,3-dimethyl-2-phenyl-1,3-dihydrobenzimidazole) in N,N-dimethylformamide at greater than 400 nm resulted in the reduction of CO2 to CO with efficiencies in the order X = OMe > tBu ≈ Me > H; Ir-CN+ has no photosensitization effect. A notable observation is that Ir-tBu+ and Ir-Me+ are less efficient than Ir-OMe+ at an early stage of the reaction but reveal persistent photosensitization behavior for a much longer period of time unlike the latter. Comparable experiments showed that (1) the Ir-X+ sensitizers are commonly superior compared to Ru(bpy)32+, a widely used transition-metal photosensitizer, and (2) the system comprising Ir-OMe+ and TiO2/ReP is much more efficient than a homogeneous-solution system using Ir-OMe+ and Re(4,4′-Y′2-bpy)(CO)3Cl (Y′ = CH2PO(OEt)2). Implications of the present observations involving reaction mechanisms associated with the different behavior of the photosensitizers are discussed in detail.

Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light

A potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase-promoted method for the synthesis of 2-substituted benzothiophenes has been developed via photoinduced intermolecular annulation of 2-halothioanisoles with terminal alkynes at ambient temperature. The present protocol uses commercially available 2-halothioanisoles as substrates and visible light as energy force, which offers a wide range of benzothiophenes regioselectively in moderate to good yields. Such a facile and effective transformation will provide an environment-friendly approach to the synthesis of benzothiophene derivatives.