42933-07-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-BROMO-2-OXO-2H-PYRAN-5-CARBOXYLATE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that possess therapeutic properties.
Used in Organic Chemistry:
In the realm of organic chemistry, METHYL 3-BROMO-2-OXO-2H-PYRAN-5-CARBOXYLATE serves as a reagent, facilitating the formation of a variety of other chemical compounds through its participation in numerous chemical reactions.
Used in Chemical Industry:
METHYL 3-BROMO-2-OXO-2H-PYRAN-5-CARBOXYLATE is utilized as a building block in the creation of diverse organic compounds, highlighting its importance in the development of new materials and substances with potential applications across various sectors.

Upstream product

• 6018-41-3 methyl coumalate 
• 500-05-0 2H-pyran-2-one-5-carboxylic acid 
• 67-56-1 methanol 

Downstream Products

• 381248-00-6 5-bromo-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid methyl ester 
• 381247-99-0 methyl 5-bromo-6-hydroxypyridine-3-carboxylate 
• 4282-28-4 2,4-furan dicarboxylic acid 
• 35029-82-4 7-bromo-1,3,6-trioxo-2-phenyl-(3at,7at)-octahydro-4r,7c-etheno-pyrano[3,4-c]pyrrole-9-carboxylic acid methyl ester 
• 41668-13-7 5-bromo-6-hydroxy-3-pyridinecarboxylic acid 
• 5043-29-8 methyl 1-bromo-3-naphthoate 
• 910875-17-1 methyl 2-bromo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carboxylate 
• 1242069-33-5 3-bromo-4-trifluoromethanesulfonyloxy-5-trimethylsilanylbenzoic acid methyl ester 
• 1242069-32-4 3-bromo-5-trifluoromethanesulfonyloxy-4-trimethylsilanyl-benzoic acid methyl ester 
• 1242069-53-9 3-bromo-5-hydroxy-4-trimethylsilanyl-benzoic acid methyl ester 
• 1242069-54-0 3-bromo-4-hydroxy-5-trimethylsilanyl-benzoic acid methyl ester 
• 1007568-97-9 C₆H₂Br(CO₂CH₃)(Si(CH₃)3)(B(OC(CH₃)2)2) 
• 1007569-02-9 C₆H₂Br(CO₂CH₃)(Si(CH₃)3)(B(OC(CH₃)2)2) 

Relevant academic research and scientific papers

[4+2] Cycloadditions between 2-pyrones and benzyne. Application to the synthesis of binaphthyls

Cycloaddition of benzyne to 2-pyrones affords the corresponding naphthalene derivatives, the intermediate bicyclic adduct not being detected. Benzopyrones do not react with benzyne under similar conditions probably because this would require the fused aromatic ring to lose aromaticity in the Diels-Alder transition state, which is therefore destabilized. 4-Bromo-2-naphthoic acid methyl ester (obtained by cycloaddition of benzyne to 3-bromo-5-carboxymethylpyran-2-one) can be transformed into 3,3'-dicarboxymethyl-1,1'-binaphthyl by Ni-mediated dimerization.

Efficient Preparation of Methyl 2-Oxo-3-aryl (heteroaryl)-2H-pyran-5-carboxylate via Pd-Catalyzed Negishi Coupling

Methyl 3-bromocoumalate, readily obtained from methyl 2-pyrone-5-carboxylate (methyl coumalate), is easily substituted by cross-coupling reactions with arylzinc reagents under palladium catalysis, leading to methyl 2-oxo-3-aryl (heteroaryl)-2H-pyran-5-carboxylates.

HETEROCYCLIC COMPOUNDS AS ANTIBIOTIC POTENTIATORS

The invention relates to heterocyclic compounds and their use as antibiotics and/or as antibiotic potentiators. The compounds may act as colistin potentiators and SOS inhibitors.

A PROCESS FOR THE PREPARATION OF 3-CYANO-1-NAPHTHOIC ACID AND SOME ANALOGUES THEREOF

The present invention is related to a process for the preparation of 3-cyano-1-naphthoic acid and some analogues thereof of formula (1), the intermediate 1-halo-3-cyano naphthalene and some analogues thereof used in this process and a process for the preparation of said intermediate.

A new route for manufacture of 3-cyano-1-naphthalenecarboxylic acid

3-Cyano-1-naphthalenecarboxylic acid is an intermediate required for manufacture of tachykinin receptor antagonists. The 1,3-disubstitution pattern on the naphthalene skeleton complicates the synthesis of this cyano acid. Previous literature-based chemistry is unattractive for large-scale manufacture due to stoichiometric use of mercury salts, low yield, and other operational difficulties. An attractive new route has been developed by establishing the 1,3-substitution on the carbon atoms destined for only one-half of the naphthalene 2-ring system, via 3-bromocoumalate, and then building up the rest of the naphthalene ring system by Diels-Alder addition of 3-bromocoumalate to in situ-generated benzyne. The resulting 4-bromo-2-naphthoate was converted to the required cyanoacid by transformation of ester to nitrile followed by carbonylation of the bromo substituent. The new route has been scaled up successfully and offers significant advantages over previous literature chemistry in terms of improved process environmental implications, improved yield, lower cost, and improved robustness and ease of operation at larger scales of operation.