942070-38-4

Usage

Uses

Used in Organic Synthesis:
1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is used as a building block for the synthesis of various pyrrole-containing compounds. Its unique structure allows for the selective and mild formation of carbon-carbon bonds, making it a valuable tool in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is used as a key intermediate for the development of novel therapeutic agents. Its pyrrole core is a common structural motif in many bioactive molecules, and its functional groups can be further modified to enhance the pharmacological properties of the resulting compounds.
Used in Agrochemical Industry:
1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is also used in the agrochemical industry for the synthesis of bioactive compounds with potential applications in crop protection and pest control. Its unique structure and reactivity make it a promising candidate for the development of new agrochemicals with improved efficacy and selectivity.
Used as a Ligand in Metal-Catalyzed Cross-Coupling Reactions:
1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid can be used as a ligand in metal-catalyzed cross-coupling reactions, facilitating the formation of carbon-carbon bonds between different organic molecules. This application expands its utility in the synthesis of complex organic compounds and contributes to the advancement of organic chemistry.
Used as a Reagent for the Functionalization of Aromatic Compounds:
Furthermore, 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid serves as a reagent for the functionalization of aromatic compounds. Its boronic acid functionality allows for the selective modification of aromatic rings, enabling the synthesis of diverse aromatic derivatives with potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 294659-30-6 methyl 1-(tert-butyloxycarbonyl)pyrrole-2-carboxylate 
• 73183-34-3 bis(pinacol)diborane 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 934-05-4 methyl 4-bromo-1H-pyrrole-2-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 156237-78-4 4-bromopyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Downstream Products

• 1198605-53-6 4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 52635-93-5 methyl 4-(2-nitrophenyl)-1H-pyrrole-2-carboxylate 
• 1413064-08-0 4-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 1287793-66-1 7-{5-(methoxycarbonyl)-1H-pyrrol-3-yl}-2-(3-fluorophenyl)-2H-[1,2,3]triazolo[4,5-f]quinoline-9-carboxylic acid 
• 1287793-23-0 7-(5-carboxy-1H-pyrrol-3-yl)-2-(3-fluorophenyl)-2H-[1,2,3]triazolo[4,5-f]quinoline-9-carboxylic acid 
• 1380306-60-4 methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate 
• 1380306-56-8 methyl 1-[3-(benzyloxy)propyl]-4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1H-pyrrole-2-carboxylate 
• 1380306-54-6 methyl 4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1-(3-hydroxypropyl)-1H-pyrrole-2-carboxylate 
• 1268621-47-1 1-tert-butyl 2-methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]-1H-pyrrole-1,2-dicarboxylate 

Relevant academic research and scientific papers

ERK INHIBITOR AND USE THEREOF

Disclosed are a compound (as shown in formula I) as an extracellular signal-regulated kinase (ERK) inhibitor, a pharmaceutical composition thereof, a preparation method therefor, and use thereof in treating ERK-mediated diseases. Said compound plays a role by regulating a plurality of processes such as cell proliferation, apoptosis, migration and angiogenesis.

Synthesis of Novel Pyrazine-Substituted 1 H -Pyrrole-2-carboxamides and Related Tethered Heterocycles

As part of a drug discovery program, 4-pyrazin-2-yl-1H-pyrrole-2-carboxamides were accessed along with a number of bicyclic analogues. Routes to these compounds were largely absent from the scientific literature. The synthesis of a 4-(pyrazin-2-yl)-1H-pyrrole-2-carboxamide and several fused bicyclic analogues all using standard procedures (SNAr, borylation, C C cross couplings, hydrolysis, amide bond formation, cyclisation, halogenation, and alkylation) from readily available starting materials is reported. The synthetic sequences range from 4-2 steps per final compound, with yields of isolated intermediates ranging from 20 to ?100%.

Discovery of a Potent and Selective Oral Inhibitor of ERK1/2 (AZD0364) That Is Efficacious in Both Monotherapy and Combination Therapy in Models of Nonsmall Cell Lung Cancer (NSCLC)

The RAS/MAPK pathway is a major driver of oncogenesis and is dysregulated in approximately 30% of human cancers, primarily by mutations in the BRAF or RAS genes. The extracellular-signal-regulated kinases (ERK1 and ERK2) serve as central nodes within this pathway. The feasibility of targeting the RAS/MAPK pathway has been demonstrated by the clinical responses observed through the use of BRAF and MEK inhibitors in BRAF V600E/K metastatic melanoma; however, resistance frequently develops. Importantly, ERK1/2 inhibition may have clinical utility in overcoming acquired resistance to RAF and MEK inhibitors, where RAS/MAPK pathway reactivation has occurred, such as relapsed BRAF V600E/K melanoma. We describe our structure-based design approach leading to the discovery of AZD0364, a potent and selective inhibitor of ERK1 and ERK2. AZD0364 exhibits high cellular potency (IC50 = 6 nM) as well as excellent physicochemical and absorption, distribution, metabolism, and excretion (ADME) properties and has demonstrated encouraging antitumor activity in preclinical models.

SUBSTITUTED 3,4-DIHYDROPYRROLO[1,2-A]PYRAZIN-1 (2H)-ONE DERIVATIVES AS KINASE INHIBITORS

Compounds of Formula (I) or pharmaceutically-acceptable salts thereof, wherein R1, R2, R3, R4, R5 and R6 have any of the meanings defined hereinbefore in the description, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of cancer are disclosed.

Synthetic strategies for the synthesis and transformation of substituted pyrrolinones as advanced intermediates for rhazinilam analogues

The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction followed by the Staudinger reaction were studied. Reacting a suitably substituted acetophenone with O-methyl O-trimethylsilyl ketene acetal gave pyrrolinones 8a and 8b in good to excellent yields. These intermediates could be transformed in four high-yielding steps into the pyrrolic precursors 7a-c containing all the atoms necessary for the construction of rings A, B, and C of rhazinilam. Our studies illustrate a lack of stability of these intermediates. Alternative synthetic approaches towards this central biaryl core structure are described.

NOVEL PYRROLE DERIVATIVES FOR THE TREATMENT OF CANCER

The invention provides a method for the treatment of cancer, which method comprises the general formula (I) wherein R1, R2, R3, R4 and W are as described herein.

Chemical synthesis of aspidosperma alkaloids inspired by the reverse of the biosynthesis of the rhazinilam family of natural products

Pyrrole reduction: Iterative metal-catalyzed C-H functionalization reactions facilitated the preparation of a highly substituted pyrrole derivative. This derivative could be transformed into the pyrrole-containing secondary metabolite, rhazinilam, which could in turn be transformed through a reductive transannular cascade process into the structurally complex pyrrolidine-containing alkaloid natural product, aspidospermidine.

Boc groups as protectors and directors for ir-catalyzed C-H borylation of heterocycles

(Chemical Equation Presented) Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions β to N. The Boc group can be removed on thermolysis