[4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone

Base Information

• Chemical Name: [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone
• CAS No.: 851590-19-7
• Molecular Formula: C₁₈H₂₃N₃O
• Molecular Weight: 297.4
• Mol file: 851590-19-7.mol

Synonyms:[4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone

Chemical Property of [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone

There total 6 articles about [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 23.0%

N-(1-methyl-4-aminopyrrole-2-carbonyl)pyrrolidine (851590-00-6) + 5-bromo-1,3-xylene (556-96-7) → [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone (851590-19-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; johnphos; sodium t-butanolate; In toluene; at 80 ℃;

DOI:10.1016/j.bmc.2005.02.019

Reference yield:

4-nitropyrrole-2-carboxylic acid (5930-93-8) → [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone (851590-19-7)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 4.5 h / 20 °C

2: 8.4 g / acetonitrile / 2 h / 0 - 20 °C

3: 94 percent / sodium hydride / dimethylformamide / 5 h / 0 - 20 °C

4: 94 percent / H₂ / Pd/C / ethyl acetate / 36 h / 20 °C

5: 23 percent / Pd₂(dba)3; 2-(di-t-butyl-phosphino)biphenyl; sodium tert-butoxide / toluene / 80 °C

With oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydrogen; sodium hydride; johnphos; sodium t-butanolate; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Buchwald coupling;

DOI:10.1016/j.bmc.2005.02.019

Reference yield:

N-(1-methyl-4-nitropyrrole-2-carbonyl)pyrrolidine (851589-99-6) → [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone (851590-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / H₂ / Pd/C / ethyl acetate / 36 h / 20 °C

2: 23 percent / Pd₂(dba)3; 2-(di-t-butyl-phosphino)biphenyl; sodium tert-butoxide / toluene / 80 °C

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydrogen; johnphos; sodium t-butanolate; palladium on activated charcoal; In ethyl acetate; toluene; 2: Buchwald coupling;

DOI:10.1016/j.bmc.2005.02.019

upstream raw materials:

N-(1-methyl-4-aminopyrrole-2-carbonyl)pyrrolidine

5-bromo-1,3-xylene

N-(4-nitropyrrole-2-carbonyl)pyrrolidine

N-(1-methyl-4-nitropyrrole-2-carbonyl)pyrrolidine

Downstream raw materials:

N-[4-[(4-acetoxybenzyl)(3,5-dimethylphenyl)amino]-1-methylpyrrole-2-carbonyl]pyrrolidine

C₂₅H₂₉N₃O

C₂₆H₃₁N₃O₂

C₂₀H₂₇N₃O