4-(3-Cyano-pyridin-2-yl)-benzoic acid ethyl ester

Base Information

• Chemical Name: 4-(3-Cyano-pyridin-2-yl)-benzoic acid ethyl ester
• CAS No.: 1208081-99-5
• Molecular Formula: C₁₅H₁₂N₂O₂
• Molecular Weight: 252.272
• Hs Code.: 2933399990
• Mol file: 1208081-99-5.mol

Synonyms:ethyl 4-(3-cyanopyridin-2-yl)benzoate

Chemical Property of 4-(3-Cyano-pyridin-2-yl)-benzoic acid ethyl ester

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

4-(3-Cyano-pyridin-2-yl)-benzoic acid ethyl ester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-Cyano-pyridin-2-yl)-benzoic acid ethyl ester

There total 3 articles about 4-(3-Cyano-pyridin-2-yl)-benzoic acid ethyl ester 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: 71.0%

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + C18H20IO2(1+)*CF3O3S(1-)*CH4 → ethyl 4-(3-cyanopyridin-2-yl)benzoate (1208081-99-5)

Guidance literature:

pyridine-3-carbonitrile; With C₉H₁₈N*Zn⁽¹⁺⁾*Cl^(1-); In tetrahydrofuran; at 50 ℃; for 1h; Schlenk technique; Inert atmosphere;

C₁₈H₂₀IO₂⁽¹⁺⁾*CF₃O₃S^(1-)*CH₄; With copper(I) trifluoromethanesulfonate * 1/2 toluene; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.6b02550

Reference yield: 69.0%

(4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride + 2-(methylthio)nicotinonitrile (219766-02-6) → ethyl 4-(3-cyanopyridin-2-yl)benzoate (1208081-99-5)

Guidance literature:

2-(methylthio)nicotinonitrile; With bis(acetylacetonate)nickel(II); bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; for 0.166667h; Inert atmosphere;

(4-(ethoxycarbonyl)phenyl)zinc(II) iodide lithium chloride; In tetrahydrofuran; at 25 ℃; for 18h; Inert atmosphere;

DOI:10.1002/chem.201002850

Reference yield:

2-chloro-3-pyridinecarbonitrile (6602-54-6) → ethyl 4-(3-cyanopyridin-2-yl)benzoate (1208081-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide / 24 h / 25 °C / Inert atmosphere

2.1: bis(acetylacetonate)nickel(II); bis[2-(diphenylphosphino)phenyl] ether / tetrahydrofuran / 0.17 h / Inert atmosphere

2.2: 18 h / 25 °C / Inert atmosphere

With bis(acetylacetonate)nickel(II); bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/chem.201002850

upstream raw materials:

2-chloro-3-pyridinecarbonitrile

2-(methylthio)nicotinonitrile

pyridine-3-carbonitrile

Refernces

• 1、 Melzig, Laurin,Metzger, Albrecht,Knochel, Paul. "Pd- and Ni-catalyzed cross-coupling reactions of functionalized organozinc reagents with unsaturated thioethers". . p. 2948 - 2956. Retrieved 2011/04/16.