93701-32-7

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dibromo-2-(bromomethyl)benzene is used as a key intermediate in the synthesis of indole derivatives, which are important in the development of pharmaceutical compounds. It is utilized in the tBuOK-promoted cyclization of imines with aryl halides, a reaction that allows for the formation of complex organic molecules with potential therapeutic applications.
Used in Medicinal Chemistry Research:
1,3-Dibromo-2-(bromomethyl)benzene is also employed in the preparation of 1,2,3,4-tetrahydro-1,8-naphthyridine derivatives. These compounds have been identified as inhibitors of αvβ6 integrin, a protein involved in various biological processes. The inhibition of this integrin has potential applications in the treatment of diseases such as cancer and fibrosis, where αvβ6 integrin plays a significant role in disease progression.

InChI:InChI=1/C7H5Br3/c8-4-5-6(9)2-1-3-7(5)10/h1-3H,4H2

Upstream product

• 69321-60-4 2,6-dibromotoluene 
• 601-84-3 2,6-dibromobenzoic acid 

Downstream Products

• 256651-54-4 C₉H₈Br₂OS 
• 97578-05-7 2,6-dibromobenzyl mercuric bromide 
• 97759-28-9 2,2',6,6'-tetrabromodibenzyl 
• 87622-66-0 bis(2,6-dibromobenzyl)mercury 
• 1147858-83-0 acetic acid 2,6-dibromobenzyl ester 
• 1380403-76-8 4-(2,6-dibromophenyl)-2-methylbutanal 
• 1380403-56-4 C₁₁H₁₄Br₂O 
• 1380403-48-4 C₁₁H₁₂Br₂ 
• 863870-92-2 4-bromo-2-phenylbenzo[b]furan 
• 1346672-58-9 2-bromo-6-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)benzyl acetate 
• 1346670-55-0 2-(3-(5-(5-(3-hydroxy-3-methylazetidin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(hydroxymethyl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 
• 1346674-91-6 2-(5-(5-(3-hydroxy-3-methylazetidin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl acetate 
• 1346670-54-9 2-(2-(hydroxymethyl)-3-(1-methyl-5-(1-(2-(methylamino)ethyl)-1H-pyrazol-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one 
• 1346674-88-1 tert-butyl 2-(3-(5-(2-(hydroxymethyl)-3-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)phenyl)-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)-1H-pyrazol-1-yl)ethyl(methyl)carbamate 

Relevant academic research and scientific papers

KRAS G12C INHIBITORS

The present invention provides compounds of the formula: where R1, R2, R3, R4, R5, A, B, and Y are as described herein, pharmaceutically acceptable salts thereof, and methods of using these compounds and salts for treating patients for cancer.

INHIBITORS OF (ALPHA-V)(BETA-6) INTEGRIN

Disclosed are small molecule inhibitors of ανβ6 integrin, and methods of using them to treat a number of diseases and conditions. Applicants have discovered novel ανβ6 integrin inhibitor compounds and evaluated the possession, performance and utility of r

tBuOK-Promoted Cyclization of Imines with Aryl Halides

A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.

INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF

Protein tyrosine phosphatases (PTPs) are key regulators of metabolism and insulin signaling. As a negative regulator of insulin signaling, the low molecular weight protein tyrosine phosphatase (LMPTP) is a target for insulin resistance and related conditions. Described herein are compounds capable of modulating the level of activity of LMPTP, compositions, and methods of using these compounds and compositions.

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

Discovery of Potent and Selective Tricyclic Inhibitors of Bruton's Tyrosine Kinase with Improved Druglike Properties

In our continued effort to discover and develop best-in-class Bruton's tyrosine kinase (Btk) inhibitors for the treatment of B-cell lymphomas, rheumatoid arthritis, and systemic lupus erythematosus, we devised a series of novel tricyclic compounds that improved upon the druglike properties of our previous chemical matter. Compounds exemplified by G-744 are highly potent, selective for Btk, metabolically stable, well tolerated, and efficacious in an animal model of arthritis.

Development of a scalable synthesis of a Bruton's tyrosine kinase inhibitor via C-N and C-C bond couplings as an end game strategy

A scalable and convergent synthesis of a BTK (Bruton's tyrosine kinase) inhibitor has been developed. Synthetic routes to key intermediates were explored for the scale-up campaign, especially the process for 6-dimethylaminodihydroisoquinolinone, which was prepared via a regioselective cyclization of an isocyanate, mediated by AlCl3. Improved routes to key building blocks were demonstrated by expedient multikilogram productions. The target compound was assembled through a Pd-catalyzed amidation reaction followed by a Suzuki-Miyaura cross-coupling reaction.

PYRIDAZINONES, METHOD OF MAKING, AND METHOD OF USE THEREOF

Pyridazinone compounds of Formula (I) including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula (I) for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

PYRIDINONES/PYRAZINONES, METHOD OF MAKING, AND METHOD OF USE THEREOF

Pyridone and pyrazinone compounds of Formula (I) including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

Atropoisomeric (P,N) ligands for the highly enantioselective Pd-catalyzed intramolecular asymmetric α-arylation of α-branched aldehydes

Three-in-one: A short synthetic route readily gives access to a new class of chiral (P,N) ligands characterized by three distinct elements of chirality. These ligands are highly enantioselective in the challenging Pd-catalyzed intramolecular asymmetric α-