34402-78-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-METHYL-1H-PYRROLE-2-CARBOXYLATE is used as a reagent for the preparation of (E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. These derivatives represent a novel class of glycine site antagonists, which are important in the development of pharmaceuticals targeting the glycine site for various therapeutic applications.
The expression for the uses of METHYL 4-METHYL-1H-PYRROLE-2-CARBOXYLATE can be summarized as follows:
Used in Pharmaceutical Industry:
METHYL 4-METHYL-1H-PYRROLE-2-CARBOXYLATE is used as a reagent for the preparation of glycine site antagonists, specifically (E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives, which have potential applications in the development of therapeutic drugs targeting the glycine site.

InChI:InChI=1/C7H9NO2/c1-5-3-6(8-4-5)7(9)10-2/h3-4,8H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 18711-59-6 4-methyl-1H-pyrrole-2-carboxylic acid 
• 77714-25-1 N-(2-methyl-3-oxoprop-1-enyl)glycine methyl ester 
• 124-41-4 sodium methylate 
• 6277-13-0 3-ethoxycarbonyl-4-methylpyrrole-2-carboxylic acid 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 1173715-82-6 methyl (2S)-4-methylene-1-p-toluenesulfonylpyrroplidine-2-carboxylate 
• 67-56-1 methanol 
• 1173715-73-5 tert-butyl (2S,4S)-4-hydroxy-4-methyl-1-p-toluenesulfonylpyrrolidine-2-carboxylate 
• 88075-95-0 1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde 
• 851590-93-7 4-methyl-pyrrole-1,2,3-tricarboxylic acid 1-tert-butyl ester 2-methyl ester 3-(2-trimethylsilanyl-ethyl) ester 
• 851590-92-6 4-methyl-1H-pyrrole-2,3-dicarboxylic acid 2-methyl ester 3-(2-trimethylsilanyl-ethyl) ester 
• 851590-94-8 4-methyl-pyrrole-1,2,3-tricarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 175235-82-2 1-Benzenesulfonyl-4-methyl-1H-pyrrole-2-carboxylic acid methyl ester 

Downstream Products

• 2243162-32-3 C₁₃H₁₀N₂O₅S 
• 2243162-67-4 C₁₉H₂₁N₃O₆S 
• 2243162-66-3 C₁₉H₂₁N₃O₆S 
• 203207-66-3 5-Isopropyl-4-methyl-3-((E)-2-phenylcarbamoyl-vinyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 18711-59-6 4-methyl-1H-pyrrole-2-carboxylic acid 

Relevant academic research and scientific papers

Phosphine-catalyzed regioselective heteroaromatization between activated alkynes and isocyanides leading to pyrroles

The organophosphine catalyzed reaction of activated alkynes with isocyanides produces the corresponding heteroaromatization products, pyrroles, regioselectively in good yields. The reaction proceeds most probably through the 1,4-addition of the nucleophil

Synthesis of alkylpyrroles by use of a vinamidinium salt

The synthesis of alkyl-substituted 2-pyrrolecarboxylate esters has been accomplished by the condensation reaction of a symmetrical vinamidinium salt and glycine ester derivatives.

Conversion of 4-oxoproline esters to 4-substituted pyrrole-2-carboxylic acid esters

The Grignard, Wittig, Tebbe, Horner-Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-su

Synthesis of 2-acyl-3-chloropyrroles: Application to the synthesis of the trail pheromone of the ant Atta texana

Alkyl 3-chloropyrrole-2-carboxylates and 2-alkanoyl-3-chloropyrroles are conveniently prepared from 2-alkyl-1-pyrrolines by tetra- and pentahalogenation with N-chlorosuccinimide, subsequent base-induced aromatisation with sodium alkoxides in the corresponding alcohol and final acid hydrolysis of the resulting orthoester or acetal functions into the 3- chloropyrrole. The developed strategy is applied to the synthesis of the trail pheromone of the ant Atta texana.

Reversible Friedel-Crafts acylations of 3-alkyl-1-(phenylsulfonyl)pyrroles: Application to the synthesis of an ant trail pheromone

Friedel-Crafts acylations of 3-alkyl-1-(phenylsulfonyl)pyrroles appear to be kinetically favored at the adjacent C-2 position but rearrangement to the C-5 position can occur after prolonged reaction times. This reversible Friedel-Crafts methodology has been employed for the synthesis of the ant trail pheromone, methyl 4-methylpyrrole-2-carboxylate.

6-Siloxy-Substituted 5,6-Dihydro-4H-1,2-oxazines as Key Building Blocks for Natural Products

Methyl (E)-5-bromo-4-oxo-2-pentenoate (6) and the corresponding oxime 5 were prepared in high yields by starting from methyl levulinate (3).The novel nitrosoalkene 8, generated in situ from oxime 5, smoothly added to silyl enol ether 7 to give 1,2-oxazine 9 and nitrone 10 as byproduct.Methods are described transforming intermediate 9 into unsaturated diketo ester 11, or oximes 13, 15, and 18, which may serve as precursors of pyrenophorin.Reductive ring cleavage of 1,2-oxazine 9 with Raney nickel efficiently afforded the saturated diketo ester 19.Its intramolecular aldol reaction gave cyclopentenone derivative 20, which is a known precursor of (Z)-jasmone.Cycloaddition of methyl α-nitrosoacrylate to silyl enol ether 22 provided 1,2-oxazine 23.This compound was directly converted into the ant-trail pheromone 24 by hexacarbonylmolybdenum-promoted ring contraction. Key Words: Pyrenophorin / (Z)-Jasmone / 1,2-Oxazine / Pheromones / Pyrroles

An Improved Synthesis of Pyrroles from N-p-Toluenesulfonylglycine Esters and α,β-Unsaturated Aldehydes and Ketones

N-p-Toluenesulfonylglycine esters 2 condensed with α,β-unsaturated carbonyl compounds 1 in the presence of the non-nucleophilic base DBU to give hydroxypyrrolidines 3.Dehydration with phosphorous oxychloride-pyridine, followed by DBU mediated elimination

Syntheses of 3-Methylpyrrole via Methyl 4-Methylpyrrole-2-carboxylate: A Thermal Oxazolone-Pyrone Rearrangement

3-Ethoxy-2-methylpropenal with hippuric acid and acetic anhydride gave 4-(3-ethoxy-2-methylallylidene)-2-phenyloxazol-5(4H)-one.By successive treatment with methanolic potassium hydroxide, acetic-hydrochloric acid, and methanolic sodium methoxide, methyl 4-methylpyrrole-2-carboxylate was formed in high overall yield, and was converted into 3-methylpyrrole by hydrolysis and decarboxylation.The oxazolone with sodium hydroxide in acetone or dioxane gave 4-(3-hydroxy-2-methylallyilidene)-2-phenyloxazol-5(4H)-one, isomerized in boiling acetone, or on melting, to 3-benzoylamino-5-methylpyran-2-one. 3-Ethoxy-2-methylpropenal condensed with glycine methyl ester to give an enaminal, cyclized in moderate yield to methyl 4-methylpyrrole-2-carboxylate.

Pyrroles from 3-Alkoxyacroleins and CH-acidic α-Aminoacetic Acid Derivatives

2-Alkoxycarbonylpyrroles and 2-cyanopyrroles 4 are prepared in a one-step synthesis by vinylogous amidation of 3-alkoxyacroleins 1 with glycine esters 2a-c and aminoacetonitrile (2d), followed by base-catalyzed cyclodehydration of the intermediate 3-aminoacroleins 3.The 3-hydroxypropyl function can be introduced into the pyrrole ring by using 3,4-dihydro-2H-pyran-5-carbaldehyde (5) as a cyclic 3-alkoxyacrolein.