82787-72-2

Usage

Uses

Used in Organic Synthesis:
6-METHYL-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a building block for the preparation of various biologically active molecules and pharmaceuticals. Its unique molecular structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Medicinal Chemistry and Drug Discovery:
In the field of medicinal chemistry, 6-METHYL-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is utilized as a precursor for the development of new drugs. Its chemical properties make it a valuable component in the design and synthesis of pharmaceutical agents targeting various diseases and conditions.
Used in Chemical Industry:
6-METHYL-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is also of interest in the chemical industry due to its potential use as a precursor for synthesizing a diverse array of functionalized compounds. Its versatile reactivity contributes to the creation of specialty chemicals for various applications.

InChI:InChI=1/C11H10O2S/c1-7-3-4-8-6-10(11(12)13-2)14-9(8)5-7/h3-6H,1-2H3

Upstream product

• 67-56-1 methanol 
• 1467-86-3 6-methyl-2-benzo[b]thiophenecarboxylic acid 
• 2365-48-2 Methyl thioglycolate 
• 146137-80-6 2-fluoro-4-methylbenzaldehyde 
• 74-88-4 methyl iodide 
• 16587-47-6 6-methylbenzo[b]thiophene 
• 352-70-5 m-Fluorotoluene 

Downstream Products

• 82787-74-4 methyl 6-(bromomethyl)benzo[b]thiophene-2-carboxylate 
• 82788-52-1 6-Imidazol-1-ylmethyl-benzo[b]thiophene-2-carboxylic acid 

Relevant academic research and scientific papers

Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives

CO2utilization is an attractive aspect as it allows the direct conversion of CO2into valuable chemicals. In this regard, direct incorporation of CO2into the C-H bond of heteroaromatic compounds is important due to the ubiquitous structural motifs of the heteroaromatic carboxylic acids. Herein, we report the Ag-catalyzed C-H carboxylation of thiophene derivatives. This new catalytic system involving a phosphine ligand and lithiumtert-butoxide enables the direct carboxylation of thiophenes under mild reaction conditions. Experimental studies revealed that the use oftert-butyl alkoxide is critical for the exergonic formation of an arylsilver intermediate, and the results were further supported by density functional theory calculations.

Discovery of a new series of potent and selective linear tachykinin NK 2 receptor antagonists

Starting from 1 (MEN 14268), a selective tachykinin NK2 receptor antagonist with an interesting in vitro pharmacological profile, a family of numerous antagonists was obtained through an optimization process focused on iterated structural modifications. The effects of the introduction of a wide variety of substituents on the lipophilic aromatic part of the molecule and the modulation of the structural constraint through the insertion of different achiral α,α-dialkylamino acids were investigated. In particular, aromatic and benzofused heteroaromatic moieties were introduced at the pseudo-N-terminal residue to replace the 2-benzothiophene moiety, and a systematic investigation of the best positioning of substituents onto the aromatic platform was reported for the benzothiophene core. Studies on the modulation of the length and the rigidity of the hydrophilic pseudo-C-terminal pendant are presented. Many heteroaliphatic groups are well tolerated by the receptor in this part of the ligand. The product 48f (MEN15596), bearing a methyl substituent on the benzothiophene and a tetrahydropyranylmethylpiperidine pendant, was finally selected for its good in vivo activity after intravenous, intraduodenal, and oral administration in guinea pigs.

Fluorine as an ortho-directing group in aromatic metalation: A two step preparation of substituted benzo[b] thiophene-2-carboxylates

A simple 2-step synthesis of B-ring substituted benzo[b]thiophene-2-carboxylates from aryl fluorides has been developed. The route involves a selective lithiation ortho to fluorine, followed by formylation, and subsequently, displacement of fluorine with