190272-33-4

Basic information

• Product Name: methyl 2-(2-methoxyphenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• Synonyms: methyl 2-(2-methoxyphenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate
• CAS NO: 190272-33-4
• Molecular Weight: 387.456
• Mol File: 190272-33-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2-(2-methoxyphenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(2-methoxyphenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate(190272-33-4)
• EPA Substance Registry System: methyl 2-(2-methoxyphenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate(190272-33-4)

Safety Data

• Hazardous Substances Data: 190272-33-4(Hazardous Substances Data)

Upstream product

• 154243-37-5 2-[(2-Methoxy-phenyl)-(toluene-4-sulfonylamino)-methyl]-acrylic acid methyl ester 
• 135-02-4 ortho-anisaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 18913-35-4 methyl buta-2,3-dienoate 
• 100200-70-2 N-(2-methoxyphenyl)methylidene-4-methylbenzenesulfonamide 
• 23326-27-4 Methyl 2-butynoate 

Downstream Products

• 190272-84-5 2-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrole-3-carboxylic acid methyl ester 
• 190273-04-2 methyl 2-(2-methoxyphenyl)-1H-pyrrole-3-carboxylate 
• 69640-32-0 2-(2-methoxyphenyl)pyrrole 
• 10245-81-5 2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol 
• 42041-50-9 2-(2-hydroxyphenyl)-1H-pyrrole 

Relevant articles and documents

Continuous flow ring-closing metathesis, an environmentally-friendly route to 2,5-dihydro-1H-pyrrole-3-carboxylates

2,5-Dihydro-1H-pyrrole-3-carboxylates are important building blocks for the synthesis of high value pyrroles and pyrroloquinoline derivatives with interesting biological activities. The use of continuous flow allowed us to perform a key synthetic step, namely ruthenium-catalyzed ring-closing metathesis, with a residence time of 1 min at 120 °C. Dimethyl carbonate, a green solvent, was demonstrated for the first time to be an excellent solvent for this reaction in continuous flow. The continuous flow conditions proved to be general and the scale-up of this reaction was not only possible, but also highly efficient. Conversion of 10 grams of diene was realized in 37 minutes under continuous flow, yielding the desired heterocycle in 91% yield.

A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin

The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates 2-butynoates with an appropriate phosphine as the catalyst, toward the electron-deficient imines is described. Triphenylphosphine-catalyzed reaction of methyl 2,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.