1109284-49-2

Usage

Uses

Used in Organic Synthesis:
Methyl 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate is used as a building block in organic synthesis for its unique reactivity and stability. The dioxaborolane group allows for versatile reactions, facilitating the creation of a wide range of complex organic molecules.
Used in Material Science:
In the field of material science, Methyl 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate is utilized for its potential to contribute to the development of new materials with specific properties. Methyl 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate's functional groups can be integrated into polymers or other materials to enhance their characteristics, such as conductivity, stability, or reactivity.
Used in Pharmaceutical Industry:
Methyl 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate is used as a precursor in the synthesis of pharmaceutical compounds. Its unique structure can be modified to create new drug candidates with potential therapeutic applications, particularly in the development of novel treatments for various diseases.
Used in Chemical Research:
In the realm of chemical research, Methyl 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate serves as a subject for studying reaction mechanisms and exploring new synthetic pathways. Its complex structure and functional groups provide opportunities for researchers to investigate its properties and reactivity, contributing to the advancement of chemical knowledge and techniques.

Upstream product

• 19432-69-0 methyl 5-methylthiophene-2-carboxylate 
• 73183-34-3 bis(pinacol)diborane 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 29421-99-6 4-bromo-5-methyl-thiophene-2-carboxylic acid 
• 237385-15-8 4-bromo-5-methylthiophene-2-carboxylic acid methyl ester 

Downstream Products

• 1314893-26-9 N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide 

Relevant academic research and scientific papers

A Suzuki Approach to Quinone-Based Diarylethene Photochromes

Diarylethene photochromes show promise for use in advanced organic electronic and photonic materials with burgeoning considerations for biological applications; however, these compounds typically require UV light for photoswitching in at least one direction, thus limiting their appeal. We here introduce a naphthoquinone-based diarylethene that switches between open and closed forms with visible light. The synthesis of this quinone diarylethene relies on Suzuki methodology, allowing for the inclusion of functional groups not otherwise accessible with current synthetic routes.

PKB inhibitor

The invention provides a PKB inhibitor, particularly relates to a compound shown as a formula I or a pharmaceutically acceptable salt thereof. The invention further provides a preparation method of the compound.

Catalyst-controlled regiodivergent C-H borylation of multifunctionalized heteroarenes by using iridium complexes

The regiodivergent C-H borylation of 2,5-disubstituted heteroarenes with bis(pinacolato)diboron was achieved by using iridium catalysts formed in situ from [Ir(OMe)(cod)]2/dtbpy (cod=1,5-cyclooctadiene, dtbpy: 4,4′-di-tert-butyl-2,2′-bipyridine) or [Ir(OMe)(cod)]2/2 AsPh3. When [Ir(OMe)(cod)]2/dtbpy was used as the catalyst, borylation at the 4-position proceeded selectively to afford 4-borylated products in high yields (dtbpy system A). The regioselectivity changed when the [Ir(OMe)(cod)]2/2 AsPh3 catalyst was used; 3-borylated products were obtained in high yields with high regioselectivity (AsPh3 system B). The regioselectivity of borylation was easily controlled by changing the ligands. This reaction was used in the syntheses of two different bioactive compound analogues by using the same starting material. Minor adjustments, major differences: The regiodivergent C-H borylation of 2,5-disubstituted heteroarenes with bis(pinacolato)diboron was achieved by using iridium catalysts formed in situ from [Ir(OMe)(cod)]2/dtbpy (cod=1,5-cyclooctadiene, dtbpy: 4,4'-di-tert-butyl-2,2'-bipyridine) or [Ir(OMe)(cod)]2/2 AsPh3 (see scheme).

Synthetic protocol for diarylethenes through Suzuki-Miyaura coupling

The synthesis of a variety of diarylethenes through the Suzuki-Miyaura coupling reaction of 1,2-dichlorohexafluorocyclopentene with arylboronic acids and esters has been developed. Thiophenes with various substituents such as cyano and ester functionalities can be incorporated.

Ester-directed regioselective borylation of heteroarenes catalyzed by a silica-supported iridium complex

Figure presented The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene, pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.

IMIDAZO[1,2-a]PYRIDINES AND IMIDAZO[1,2-b]PYRIDAZINES AS MARK INHIBITORS

The invention encompasses imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine derivatives which selectively inhibit microtubule affinity regulating kinase (MARK) and are therefore useful for the treatment or prevention of Alzheimer's disease. Pharmaceutical compositions and methods of use are also included.

PYRAZOLO[1,5-A]PYRIDINES AS MARK INHIBITORS

The invention encompasses pyrazolo[1,5-a]pyridine derivatives which selectively inhibit microtubule affinity regulating kinase (MARK) and are therefore useful for the treatment or prevention of Alzheimer's disease. Pharmaceutical compositions and methods of use are also included.

PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES

Compounds of the following formula (I) are inhibitors of microtubule affinity regulating kinase, and hence find use in the treatment of neurodegenerative diseases associated with hyperphosphorylation of tau.