ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

Base Information

Chemical Name:ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate
CAS No.:894075-10-6
Molecular Formula:C₂₃H₁₉ClN₄O₂
Molecular Weight:418.882
Hs Code.:

Synonyms:ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

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Chemical Property of ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

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Technology Process of ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

There total 9 articles about ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-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: 64.0%

: 562072-83-7
4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

: 894074-87-4
ethyl 5-(bromomethyl)-2-chloropyridine-3-carboxylate

: 894075-10-6
ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

Guidance literature:: 4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.25h;

ethyl 5-(bromomethyl)-2-chloropyridine-3-carboxylate; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 1.5h;
DOI:10.1016/j.bmc.2011.10.067

Reference yield:

: 69687-80-5
methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate

: 894075-10-6
ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridinium hydrobromide perbromide; triethylamine / dichloromethane / 2 h / 0 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 1 h / 0 °C

3.2: brine

4.1: thionyl chloride / tetrahydrofuran / 1 h / 20 °C

5.1: ammonium hydroxide / tetrahydrofuran / 1 h / 20 °C

6.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C

7.2: 1.5 h / 20 °C

With pyridine; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; oxalyl dichloride; pyridinium hydrobromide perbromide; boron tribromide; sodium hydride; sodium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 2.1: Suzuki coupling;
DOI:10.1016/j.bmc.2011.10.067

Reference yield:

: 4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxamide

: 894075-10-6
ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine; oxalyl dichloride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C

2.2: 1.5 h / 20 °C

With pyridine; oxalyl dichloride; sodium hydride; In N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.bmc.2011.10.067