ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

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Chemical Name:ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate
CAS No.:1370023-00-9
Molecular Formula:C₁₉H₁₈ClN₃O₂
Molecular Weight:355.824
Hs Code.:

Synonyms:ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

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Chemical Property of ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

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Technology Process of ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

There total 4 articles about ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate 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: 83.0%

: 14918-21-9
5-hexynonitrile

: 1370022-90-4
ethyl 5-(3-chlorophenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate

: 1370023-00-9
ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

Guidance literature:: ethyl 5-(3-chlorophenyl)-4-iodo-1-methyl-1H-pyrazole-3-carboxylate; With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; In ethanol; at 25 - 30 ℃; for 0.5h; Inert atmosphere;

5-hexynonitrile; In ethanol; at 20 - 70 ℃; Inert atmosphere;
DOI:10.1016/j.bmcl.2012.02.008

Reference yield:

: 1370022-89-1
ethyl 5-(3-chlorophenyl)-4-iodo-1H-pyrazole-3-carboxylate

: 1370023-00-9
ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.08 h / 0 °C / Inert atmosphere

1.2: 0.25 h / Inert atmosphere

2.1: copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine / ethanol / 0.5 h / 25 - 30 °C / Inert atmosphere

2.2: 20 - 70 °C / Inert atmosphere

With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; potassium hydroxide; In ethanol; N,N-dimethyl-formamide; 2.1: Sonogashira coupling / 2.2: Sonogashira coupling;
DOI:10.1016/j.bmcl.2012.02.008

Reference yield:

: 57961-48-5
ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

: 1370023-00-9
ethyl 5-(3-chlorophenyl)-4-(5-cyanopent-1-ynyl)-1-methyl-1H-pyrazole-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic acid; hydrazine / 10 h / 120 - 125 °C / Inert atmosphere

2.1: ammonium cerium (IV) nitrate; iodine / acetonitrile / 3 h / 50 °C / Inert atmosphere

3.1: potassium hydroxide / N,N-dimethyl-formamide / 0.08 h / 0 °C / Inert atmosphere

3.2: 0.25 h / Inert atmosphere

4.1: copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine / ethanol / 0.5 h / 25 - 30 °C / Inert atmosphere

4.2: 20 - 70 °C / Inert atmosphere

With copper(l) iodide; ammonium cerium (IV) nitrate; palladium 10% on activated carbon; iodine; acetic acid; triethylamine; triphenylphosphine; potassium hydroxide; hydrazine; In ethanol; N,N-dimethyl-formamide; acetonitrile; 4.1: Sonogashira coupling / 4.2: Sonogashira coupling;
DOI:10.1016/j.bmcl.2012.02.008