490035-82-0

Usage

Uses

Used in Organic Synthesis:
Methyl 3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is used as a building block in organic synthesis for the production of pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile reactivity and structural properties make it a valuable component in the synthesis of various complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is used as a key intermediate in the synthesis of various drug molecules. Its unique structure and reactivity enable the development of new pharmaceutical compounds with improved therapeutic properties.
Used in Agrochemical Industry:
Methyl 3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is also utilized in the agrochemical industry as a building block for the synthesis of various agrochemical products, such as pesticides and herbicides. Its versatile reactivity allows for the development of new agrochemicals with enhanced efficacy and selectivity.
Used in the Development of New Materials:
Methyl 3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is used in the development of new materials with unique properties. Its structural properties and reactivity make it a valuable component in the creation of advanced materials for various applications, such as in electronics, coatings, and composites.

Upstream product

• 75567-84-9 methyl 3-(4-bromopehynl)propanoate 
• 73183-34-3 bis(pinacol)diborane 
• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 4489-23-0 4-bromo-β-methylstyrene 
• 25574-11-2 3-(4-bromophenyl)propanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 33994-44-4 3-(4-iodophenyl)propionic acid methyl ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 4489-22-9 (+/-)-1-(4-bromophenyl)propanol 

Downstream Products

• 1421230-74-1 methyl 3-(4-(4-(methylthio)thieno[3,2-d]pyrimidin-7-yl)phenyl)propanoate 
• 1402466-07-2 (R)-3-(4'-(5-(((1-(2-chlorophenyl)ethoxy)carbonyl)amino)-1-methyl-1H-pyrazol-4-yl)-[1,1'-biphenyl]-4-yl)propanoic acid methyl ester 

Relevant academic research and scientific papers

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Para-selective borylation of monosubstituted benzenes using a transient mediator

Herein, we conceptualized a transient mediator approach that has the capability of para-selective C-H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.

Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?

Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.

Indazole-6-phenylcyclopropylcarboxylic Acids as Selective GPR120 Agonists with in Vivo Efficacy

GPR120 agonists have therapeutic potential for the treatment of diabetes, but few selective agonists have been reported. We identified an indazole-6-phenylcyclopropylcarboxylic acid series of GPR120 agonists and conducted SAR studies to optimize GPR120 potency. Furthermore, we identified a (S,S)-cyclopropylcarboxylic acid structural motif which gave selectivity against GPR40. Good oral exposure was obtained with some compounds displaying unexpected high CNS penetration. Increased MDCK efflux was utilized to identify compounds such as 33 with lower CNS penetration, and activity in oral glucose tolerance studies was demonstrated. Differential activity was observed in GPR120 null and wild-type mice indicating that this effect operates through a mechanism involving GPR120 agonism.

PROCESSES FOR THE PREPARATION OF BIPHENYL COMPOUNDS

The invention concerns processes for the synthesis of a compound of the formula: wherein: R1 and R2 are each, independently, C1-C12 alkyl, CO2R3, OR4, R5(OR6), or C6-C18 aiyl; R3 -R6 are each, independently, C1-C12 alkyl or C6-C12 aryl; and n and m are each, independently, O or an integer from 1-5; said process comprising: — contacting a compound of the formula H0-R7-0H with BH3 and a compound of the formula in the presence of a nickel-containing catalyst to produce a first product, where R7 is a C2-C12 hydrocarbon group and X is a halogen, OMs or OTs; — contacting the first product in situ with a compound of the formula: in the presence of a nickel-containing catalyst to produce a compound of formula I, where Z is a halogen.

Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane

(Chemical Equation Presented) A procedure for NiCl2(dppp)- catalyzed pinacolborylation and neopentylglycolborylation that utilizes in situ prepared inexpensive pinacolborane and neopentylglycolborane is reported. The scope of this reaction was demonstrated with a variety of aryl bromides and iodides. The resulting aryl neopentylglycolboronic esters undergo a NiCl 2(dppe)-catalyzed cross-coupling with aryl halides, resulting in an extremely efficient and cost-effective method for the synthesis of functional biaryls, dendritic building blocks, and other complex architectures.

VITAMIN D-LIKE COMPOUND

The present invention provides a compound represented by the following general formula (I): or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing such a compound, and the like. The compound or a pharmaceutically acceptable

Syntheses with organoboranes. XIII. Synthesis of ω-(4-bromophenyl)alkanoic acids and their borylation

ω-(4-Bromophenyl)alkanoic acids 2c-e were obtained from 1-bromo-4-alkenylbenzenes 5c-e by hydroboration-thermal isomerization-oxidation. Their esters 11c-e were transformed in good yields into the corresponding boronates 12c-e by the cross-coupling reaction with (10) in an ionic liquid, [bmim][BF4]. The use of pinacolborane for the coupling reaction in the ionic liquid gave debromination products, and low yields of 12c-e. Ethyl 3-(4-bromophenyl)propanoate (7c) was transformed into ethyl 3-(4-[1,3,2]dioxaborolanyl)propanoate (9c) by the cross-coupling with [2,2′]bi[[1,3,2]dioxaborinanyl].