52074-58-5

Upstream product

• 64-17-5 ethanol 
• 85380-92-3 1-(methylsulfinyl)-1-methylthio-2-(1-methyl-5-p-toluoyl-2-pyrrolyl)ethylene 
• 96-54-8 N-Methylpyrrole 
• 3278-34-0 ethyl 2-(ethoxythiocarbonylthio)acetate 
• 62128-31-8 (1-methyl-1H-pyrrol-2-yl)-p-tolylmethanone 
• 83863-74-5 2-(carboxymethyl)-1-methyl-1H-pyrrole-3-carboxylic acid 
• 94133-60-5 C₁₀H₁₃NO₄ 
• 49669-45-6 ethyl (1-methyl-1H-pyrrol-2-yl)acetate 
• 874-60-2 4-methyl-benzoyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 6279-86-3 methanetricarboxylic acid triethyl ester 
• 55895-62-0 2-(4-methylbenzoyl)pyrrole 
• 52074-60-9 (5-chlorocarbonyl-1-methyl-pyrrol-2-yl)-acetic acid ethyl ester 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 26171-23-3 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid 

Relevant academic research and scientific papers

Synthetic method of non-steroidal antiinflammatory drug pain killing

The invention discloses a synthesis method of non-steroidal anti-inflammatory drug tolmetin. The methodcomprises the following steps: sequentially preparing a sulfuric acid-containing acetonedicarboxylic acid crude product, 2-(2-acetoxy)-1-methyl-1H-pyrrole-3-formic acid and 2-(2-alkyl acetate)-1-methyl-1H-pyrrole-3-formic acid by taking citric acid or citric acid monohydrate as a raw material; and carrying out decarboxylation, acylation, hydrolysis and acidification to obtain tolmetin. The synthetic method provided by the invention overcomes the defect that the existing tolmetin preparation process depends on N-methylpyrrole, and is a low-cost, low-pollution and high-yield synthetic method of non-steroidal anti-inflammatory drug tolmetin.

Selective PdII-Catalyzed Acylation of Pyrrole with Aldehydes. Application to the Synthesis of Celastramycin Analogues and Tolmetin

The PdII-catalyzed C-2 acylation of pyrrole with aldehydes in the presence of TBHP as oxidant has been studied for the synthesis of di(hetero)aryl ketones. The use of 2-pyrimidine as directing group leads to 2-acylpyrroles in moderate to good yields, although 2,5-diacylpyrroles are obtained as by products. This side-reaction could be avoided using 3-methy-2-pyridine as directing group, obtaining selectively 2-acylpyrroles. The reaction has been extended to a series of aromatic and heteroaromatic aldehydes, obtaining the best results with electron rich aromatic aldehydes. The methodology has been applied in the synthesis of pyrrolomycin alkaloid Celastramycin analogues and for an improved synthesis of Tolmetin, a nonsteroidal anti-inflammatory drug.

Solvent free oxidative radical substitution process. Synthesis of pyrrole fused systems

A xanthate-based, solvent free, homolytic substitution on selected substituted pyrrole systems is described. Additionally, a practical entry for the rapid construction of pyrrole fused systems using this solventless radical addition followed by a double nucleophilic alkylation sequence, is also reported.

Synthesis and reaction of chiral 4,5-disubstituted 2-oxazolidinones from 3-ethoxy-6-(N-alkyl-N-tert-butoxy- carbonyl)aminohexa-2,4-dienoates in the presence of concentrated sulfuric acid supported on silica gel

Reaction of chiral 3-ethoxy-6-(N-alkyl-N-tert-butoxycarbonyl)amino-hexa- 2,4-dienoates (3) and related compounds with 97% concentrated sulfuric acid supported on silica gel proceeded stereo- and regio-selectively to yield chiral 4,5-disubstituted N-alkyl-2-oxazolidinones (7). Under the limited conditions, 7 were converted into N-alkyl-2-pyrrolylacetates (8) and 2- oxazolidinone derivatives (12) which may serve as a chiral auxiliary.

Homolytic aromatic substitutions of pentatomic heteroaromatics with electrophilic carbon radicals generated by alkyl halides and triethylborane

An efficient homolytic aromatic substitution of pyrroles, furan and thiophene by ·CH2CO2Et and ·CH(CH3)CO2Et has been carried out the radicals being generated by autoxidation of BEt3 in the presence of XCH2CO2Et and XCH(CH3)CO2Et(X=Br, I).

Non-steroidal antiinflammatory agents. 1. A novel synthesis of 1-methyl-5-p-tolylpyrrole-2-acetic acid (tolmetin)

A four-step preparation of 1-methyl-5-p-tolylpyrrole-2-acetic acid (Tolmetin) is reported starting from 1-methyl-2-p-tolylpyrrole. Formylation of this compound followed by condensation with methyl(methylthio)methyl sulfoxide furnished 1-(methylsulfinyl)-1-methylthio-2-(1-methyl-5-p-tolyl-2-pyrrolyl)ethylene. Pummerer rearrangement of the latter compound gave ethyl 1-methyl-5-p-tolypyrrole-2-acetate, which was hydrolyzed in alkaline medium to afford Tolmetin.

5-Chlorocarbonyl

A process of preparing certain 5-aroyl-pyrrole-2-alkanoic acid derivatives using phosgene and certain 5-unsubstituted pyrroles as starting materials, and certain novel 5-chlorocarbonyl-pyrrole precursors.