253280-01-2

Upstream product

• 766-51-8 2-Chloroanisole 
• 578-57-4 2-bromoanisole 
• 90-04-0 2-methoxy-phenylamine 
• 67-56-1 methanol 
• 121-43-7 Trimethyl borate 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 100-66-3 methoxybenzene 

Downstream Products

• 190788-60-4 pinacol 2-anisylboronate 
• 508209-77-6 methyl 3-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate 
• 508209-71-0 methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-69-6 methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-72-1 methyl {3-[5-(3-aminopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-70-9 methyl {3-[5-(3-bromopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 724700-58-7 {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid 
• 173204-11-0 methyl 3-<2-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy>phenyl>phenylacetate 
• 5720-06-9 2-Methoxyphenylboronic acid 

Relevant academic research and scientific papers

Amine-borane complexes: Air- and moisture-stable partners for palladium-catalyzed borylation of aryl bromides and chlorides

A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.

Method for preparing aminoarylborane compounds or derivatives thereof

The present invention provides a process for the preparation of aminoarylborane compounds and derivatives thereof comprising a step of arylation by reacting an aryl chloride with an aminoborane compound in the presence of a catalytic system. Typically, th

Borylation using group IV metallocene under mild conditions

A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway.

Synthesis of phenylboronic acids in continuous flow by means of a multijet oscillating disc reactor system operating at cryogenic temperatures

A multijet oscillating disk (MJOD) millireactor system suitable for operating at cryogenic temperatures has been developed, assembled, and investigated. This new reactor system (cryoMJOD) was realized with the purpose to prepare various phenylboronic acids in a continuous two (three)-step telescoped synthetic process at temperatures in the interval -50 to -75 °C. In this process, n-butyllithium was reacted with a phenylbromide to provide the corresponding phenyllithium derivative, whereupon a borate was added under the formation of target product phenylboronic acid in good selectivity and medium-to-good yield (50-75%). These results were competitive with results previously revealed in the literature. The residence times of the telescoped two-step process were considerably shorter compared to those of batch mode operations for the identical syntheses. The flow process was optimized by means of statistical experimental design and multivariate regression, upon which the process was utilized for the production of a series of phenylboronic acid derivatives, all in medium-to-good yield. One of the substrates, 4-methoxyphenylboronic acid, was submitted for throughput improvements, resulting in a process with capability to produce the product phenylboronic acid in a quantity of 2.0 kg × day-1.

Mild and selective synthesis of an aryl boronic ester by equilibration of mixtures of boronic and borinic acid derivatives

Quenching of aryl Grignard reagents with 2-isopropoxy-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (isopropyl pinacol borate) under noncryogenic conditions can lead to mixtures of the corresponding boronic ester along with, generally undesired, borinic acid derivatives. We have found that in certain cases gentle heating of the crude reaction mixtures leads to complete equilibration to give the borinic esters as the sole product which can then be isolated in high yield. This novel equilibration can reduce the need for use of cryogenic conditions or large excesses of reagents to obtain selectivity during boronic ester syntheses.

Synthesis of a Sialyl LewisX mimetic conjugated with DTPA, potential ligand of new contrast agents for medical imaging

The structure of a mimetic of sialyl LewisX, namely 3-[2-(α-D-mannopyranosyloxy)phenyl]phenylacetic acid, was coupled to diethylenetriaminepentaacetic acid (DTPA) via a flexible alkyl spacer and the amide linkage. The overall yield of the eleven-step synthesis starting from 3-bromophenylacetic acid was 4-8%. This new ligand is expected to target inflammation sites through specific interactions with selectins, the adhesion molecules expressed on the vascular endothelium in pathological conditions. In particular, complexation of the DTPA moiety with gadolinium or radionuclides could produce contrast agents for medical imaging. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Substituted 3-amino biaryl propionic acids as potent VLA-4 antagonists.

A series of substituted N-(3,5-dichlorobenzenesulfonyl)-(L)-prolyl- and (L)-azetidyl-beta-biaryl beta-alanine derivatives was prepared as selective and potent VLA-4 antagonists. The 2,6-dioxygenated biaryl substitution pattern is important for optimizing potency. Oral bioavailability was variable and may be a result of binding to circulating plasma proteins.