26563-22-4

Upstream product

• 27884-09-9 2-(4-methoxyphenyl)benzo[b]thiophene 
• 84904-70-1 1-((4-methoxyphenyl)ethynyl)-2-(methylsulfanyl)benzene 
• 33775-94-9 2-(methylthio)iodobenzene 
• 768-60-5 4-methoxyphenylacetylen 
• 78905-08-5 <(o-methylthio)phenyl>acetylene 
• 415680-02-3 trimethyl{[2-(methylsulfanyl)phenyl]ethynyl}silane 
• 7342-82-7 3-Bromothianaphthene 
• 696-62-8 para-iodoanisole 
• 95-15-8 Benzo[b]thiophene 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 6163-58-2 tris-(o-tolyl)phosphine 

Downstream Products

• 13400-02-7 3,4,5-trimethoxy styrene 
• 193964-32-8 methyl 4-[[2-(4-methoxyphenyl)benzo[b]thiophen-3-yl]thio]phenyl ether 
• 193964-33-9 4-[[2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl]thio]phenol 

Relevant academic research and scientific papers

Synthesis of novel benzo[ b ]furans and benzo[ b ]thiophenes: Analogs of combretastatin and resveratrol

A rapid and efficient synthesis of fused polyphenolic/polymethoxy benzofurans and benzothiophenes that have potential as antitumor agents and components of anti-HIV combination therapy has been achieved.

Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes

An efficient and practical protocol for the Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles towards valuable 3-halobenzo[b]thiophenes is described. Structurally diverse 3-halobenzothiophenes were obtained in good to excellent yields

Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System

A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO3Na or Pd/MeDavephos-CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.

Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes

A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed met

Synthesis of a 3-(α-Styryl)benzo[ b ]-thiophene Library via Bromocyclization of Alkynes and Palladium-Catalyzed Tosylhydrazones Cross-Couplings: Evaluation as Antitubulin Agents

A library of functionalized 3-(α-styryl)-benzo[b]thiophenes, endowed with a high level of molecular diversity, was efficiently synthesized by applying a synthetic sequence that allowed introduction of various substituents on aromatic A, B, and C-rings. Th

Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS

A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.

MPHT-Promoted bromocyclization of of ortho-substituted arylalkynes: Application to the synthesis of 2-substituted 3-bromobenzofurans and -benzo[b]thiophenes

A convenient: and general approach to the synthesis of 2substituted 3-bromobenzofurans and -benzothiophenes was developed. The procedure is based, on the cyclization of orfho-substituted arylalkynes in the presence of N-methylpyrrolidin-2-one hydrotribromide (MPHT) as a soft and easy-tohandle electrophilic brominating reagent. Under mild reaction conditions, MPHT promoted the bromocyclization of various enynes and diynes as well as arylalkynes to give 2substituted 3-bromobenzofurans and -benzothiophenes in. high to excellent: yields. Subsequent: functionalization by palladium-catalyzed coupling reactions at the C-Br bond afforded general access to 2,3-disubstituted benzofurans and benzothiophenes of biological interest.

Halocyclization of 2-alkynylthioanisoles by cupric halides: synthesis of 2-substituted 3-halobenzo[b]thiophenes

Reaction of 2-alkynylthioanisoles 3 with 2 equiv of CuX2 (X=Br or Cl) in refluxing CH3CN for 2.5 h gave the 2-substituted 3-halobenzo[b]thiophenes 4 in good yields.

Diamino benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 5. Potency, efficacy, and pharmacokinetic properties of modified C-3 side chain derivatives

A systematic investigation of the structure-activity relationships of the C-3 side chain of the screening hit la led to the identification of the potent thrombin inhibitors 23c, 28c, and 31c. Their activities (1240, 903, and 1271 x 106 L/mol, respectively) represent 2200- and 2900-fold increases in potency over the starting lead la. This activity enhancement was accomplished with an increase of thrombin selectivity. The in vitro anticoagulant profiles of derivatives 28c and 31c were determined, and they compare favorably with the clinical agent H-R-1-[4aS,- 8aS]perhydroisoquinolyl-prolyl-arginyl aldehyde (D-Piq-Pro-Arg-H; 32). The more potent members of this series have been studied in an arterial/venous shunt (AV shunt) model of thrombosis and were found to be efficacious in reducing clot formation. However, their efficacy is currently limited by their rapid and extensive distribution following administration.

Benzothiophene compounds as antithrombotic agents and intermediates

This application relates to novel compounds of formula I (and their pharmaceutically acceptable salts), as defined herein, processes and intermediates for their preparation, pharmaceutical formulations comprising the novel compounds of formula I, and the