ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate

Base Information

• Chemical Name: ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate
• CAS No.: 1208318-09-5
• Molecular Formula: C₂₃H₂₃BrN₂O₃
• Molecular Weight: 455.351
• Mol file: 1208318-09-5.mol

Synonyms:ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate

Chemical Property of ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate

There total 9 articles about ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate 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: 61.0%

ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate (1208318-08-4) + 4-amino-3-methylbenzamide (106037-36-9) → ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (1208318-09-5)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; Reflux;

Reference yield:

3-methyl-4-(1H-pyrrol-1-yl)benzamide (1208318-10-8) → ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (1208318-09-5)

Guidance literature:

Multi-step reaction with 6 steps

1: trichlorophosphate

2: toluene / Reflux

3: palladium 10% on activated carbon; hydrogen / ethanol

4: N-Bromosuccinimide

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate

6: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 20 °C

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; sodium carbonate; potassium carbonate; trichlorophosphate; In ethanol; dimethyl sulfoxide; toluene; 1: Vilsmeier formylation / 2: Wittig reaction / 5: Suzuki coupling;

DOI:10.1021/ml200045s

Reference yield:

4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile (1208318-11-9) → ethyl 3-(5-(4-bromophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl)propanoate (1208318-09-5)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / Reflux

2: palladium 10% on activated carbon; hydrogen / ethanol

3: N-Bromosuccinimide

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate

5: dihydrogen peroxide; potassium carbonate / dimethyl sulfoxide / 20 °C

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; sodium carbonate; potassium carbonate; In ethanol; dimethyl sulfoxide; toluene; 1: Wittig reaction / 4: Suzuki coupling;

DOI:10.1021/ml200045s

upstream raw materials:

3-methyl-4-(1H-pyrrol-1-yl)benzamide

4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile

ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)acrylate

ethyl 3-(5-bromo-1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)propanoate

Downstream raw materials:

3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrole -2-yl)propionic acid

3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(2-methyl-4-(methylsulfonamido)phenyl)-1H-pyrrol-2-yl)propanoic acid

3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-amino-2-methylphenyl)-1H-pyrrol-2-yl)propanoic acid

ethyl 3-(5-(4-(1H-imidazol-1-yl)phenyl)-1-(4-(aminomethyl)-2-methylphenyl)-1H-pyrrol-2-yl)propanoate

Refernces

• 1、 Sun, Xicheng,Wasley, Jan W. F.,Qiu, Jian,Blonder, Joan P.,Stout, Adam M.,Green, Louis S.,Strong, Sarah A.,Colagiovanni, Dorothy B.,Richards, Jane P.,Mutka, Sarah C.,Chun, Lawrence,Rosenthal, Gary J.. "Discovery of S-nitrosoglutathione reductase inhibitors: Potential agents for the treatment of asthma and other inflammatory diseases". . p. 402 - 406. Retrieved 2011/06/26.