methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate

Base Information

• Chemical Name: methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate
• CAS No.: 1377495-54-9
• Molecular Formula: C₁₇H₁₈N₂O₂
• Molecular Weight: 282.342
• Mol file: 1377495-54-9.mol

Synonyms:methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate

Chemical Property of methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate

There total 6 articles about methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate 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: 97.0%

2-iodophenylamine (615-43-0) + methyl 4-(1H-pyrrol-1-yl)hex-5-ynoate (1377495-51-6) → methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate (1377495-54-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; In N,N-dimethyl-formamide; at 70 ℃; for 1h; Microwave irradiation;

DOI:10.1055/s-0031-1289745

Reference yield:

methyl 5-oxo-4-(1H-pyrrol-1-yl)pentanoate (1377495-40-3) → methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate (1377495-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / methanol / 8 h / 20 °C / Inert atmosphere

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 1 h / 70 °C / Microwave irradiation

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; diethylamine; In methanol; N,N-dimethyl-formamide; 2: Sonogashira coupling;

DOI:10.1055/s-0031-1289745

Reference yield:

5-methoxy-5-oxo-2-(1H-pyrrol-1-yl)pentanoic acid (1377495-45-8) → methyl 6-(2-aminophenyl)-4-(1H-pyrrol-1-yl)hex-5-ynoate (1377495-54-9)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2: triethylamine / 3.5 h / 0 °C

3: triethylsilane; palladium 10% on activated carbon / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

4: potassium carbonate / methanol / 8 h / 20 °C / Inert atmosphere

5: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 1 h / 70 °C / Microwave irradiation

With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; palladium 10% on activated carbon; potassium carbonate; diethylamine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Sonogashira coupling;

DOI:10.1055/s-0031-1289745

upstream raw materials:

DL-glutamic acid-5-methyl ester

methyl 5-oxo-4-(1H-pyrrol-1-yl)pentanoate

5-methoxy-5-oxo-2-(1H-pyrrol-1-yl)pentanoic acid

methyl 5-(ethylthio)-5-oxo-4-(1H-pyrrol-1-yl)pentanoate

Downstream raw materials:

5-[(2-aminophenyl)ethynyl]-6,7-dihydroindolizin-8(5H)-one