tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate

Base Information

• Chemical Name: tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate
• CAS No.: 1284183-66-9
• Molecular Formula: C₂₉H₃₂ClN₃O₆
• Molecular Weight: 554.043
• Mol file: 1284183-66-9.mol

Synonyms:tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate

Chemical Property of tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate

There total 7 articles about tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)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: 98.0%

methyl 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-iodophenyl(methoxy)carbamate (1284183-64-7) + hex-5-ynoic acid tert-butyl ester (73448-14-3) → tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate (1284183-66-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 4.5h; Inert atmosphere;

DOI:10.1039/c0ob00686f

Reference yield:

1-(4-chlorophenyl)-3-pyrazolidinone (6119-12-6) → tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate (1284183-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxygen; copper(l) chloride / N,N-dimethyl-formamide / 3 h / 20 °C

1.2: 1 h

2.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxygen; caesium carbonate; triethylamine; copper(l) chloride; In N,N-dimethyl-formamide; 3.1: Sonogashira coupling;

DOI:10.1039/c0ob00686f

Reference yield:

methyl N-(2-methylphenyl)-N-methoxy-carbamate (151827-82-6) → tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hex-5-ynoate (1284183-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: iodine; silver sulfate / acetic acid / 20 h / 20 °C / Darkness

2: bromine / tetrachloromethane / 36 h / 20 °C / Irradiation

3: caesium carbonate / N,N-dimethyl-formamide / 20 °C

4: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; bromine; iodine; caesium carbonate; silver sulfate; triethylamine; In tetrachloromethane; acetic acid; N,N-dimethyl-formamide; 4: Sonogashira coupling;

DOI:10.1039/c0ob00686f

upstream raw materials:

methyl N-(2-methylphenyl)-N-methoxy-carbamate

1-(para-chlorophenyl)-3-hydroxypyrazole

methyl 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-iodophenyl(methoxy)carbamate

hex-5-ynoic acid tert-butyl ester

Downstream raw materials:

tert-butyl 6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hexanoate

6-(3-((1-(4-chlorophenyl)-1H-pyrazol-3-yloxy)methyl)-4-(methoxy(methoxycarbonyl)amino)phenyl)hexanoic acid