1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

Base Information

Chemical Name:1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile
CAS No.:894073-97-3
Molecular Formula:C₂₁H₁₇ClN₄O
Molecular Weight:376.845
Hs Code.:

Synonyms:1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

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Chemical Property of 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

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Technology Process of 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

There total 10 articles about 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile 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: 78.0%

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

: 894073-97-3
1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

Guidance literature:: ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate; With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 14h;

With citric acid; In tetrahydrofuran; ethanol; water; at 20 ℃;
DOI:10.1016/j.bmc.2011.10.067

Reference yield:

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

: 894073-97-3
1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

Guidance literature:: Multi-step reaction with 8 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

8.1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol / 14 h / 20 °C

8.2: 20 °C

With pyridine; ammonium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; oxalyl dichloride; pyridinium hydrobromide perbromide; boron tribromide; sodium hydride; sodium carbonate; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; 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

: 894073-97-3
1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile

Guidance literature:: Multi-step reaction with 3 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

3.1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol / 14 h / 20 °C

3.2: 20 °C

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