Benzenepropanoic acid, 3-[2-[[(4-fluorophenyl)sulfonyl]amino]ethyl]-5-(3-pyridinylmethyl)-, ethyl ester

Base Information

• Chemical Name: Benzenepropanoic acid, 3-[2-[[(4-fluorophenyl)sulfonyl]amino]ethyl]-5-(3-pyridinylmethyl)-, ethyl ester
• CAS No.: 145690-73-9
• Molecular Formula: C25H27FN2O4S
• Molecular Weight: 470.565
• Mol file: 145690-73-9.mol

Synonyms:

Chemical Property of Benzenepropanoic acid, 3-[2-[[(4-fluorophenyl)sulfonyl]amino]ethyl]-5-(3-pyridinylmethyl)-, ethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanoic acid, 3-[2-[[(4-fluorophenyl)sulfonyl]amino]ethyl]-5-(3-pyridinylmethyl)-, ethyl ester

There total 10 articles about Benzenepropanoic acid, 3-[2-[[(4-fluorophenyl)sulfonyl]amino]ethyl]-5-(3-pyridinylmethyl)-, 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:

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → ethyl 3-{3-[2-(4-fluorophenylsulphonylamino)ethyl]-5-(pyridin-3-ylmethyl)phenyl}propanoate (145690-73-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 30 min, 2.) ether, hexane, from -78 deg C to 0 deg C

2: 1.) N₂H₄*H₂O, ethylene glycol, 2.) KOH / 1.) reflux, 45 min, 2.) reflux, 30 min

3: 83 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 1 h / Heating

4: 95 percent / HCO₂NH₄ / 10percent Pd/C / ethanol; tetrahydrofuran / 1 h / 60 °C

5: 43 percent / aq. NaOH / ethanol / 0.75 h / Heating

6: diphenyl phosphorazidate, Et₃N / 18 h / Heating

7: TFA / CH₂Cl₂ / 4 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

With palladium diacetate; potassium hydroxide; sodium hydroxide; n-butyllithium; diphenyl phosphoryl azide; ammonium formate; hydrazine hydrate; ethylene glycol; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

Reference yield:

1,3,5-trisbromobenzene (626-39-1) → ethyl 3-{3-[2-(4-fluorophenylsulphonylamino)ethyl]-5-(pyridin-3-ylmethyl)phenyl}propanoate (145690-73-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 30 min, 2.) ether, hexane, from -78 deg C to 0 deg C

2: 1.) N₂H₄*H₂O, ethylene glycol, 2.) KOH / 1.) reflux, 45 min, 2.) reflux, 30 min

3: 83 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 1 h / Heating

4: 95 percent / HCO₂NH₄ / 10percent Pd/C / ethanol; tetrahydrofuran / 1 h / 60 °C

5: 43 percent / aq. NaOH / ethanol / 0.75 h / Heating

6: diphenyl phosphorazidate, Et₃N / 18 h / Heating

7: TFA / CH₂Cl₂ / 4 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

With palladium diacetate; potassium hydroxide; sodium hydroxide; n-butyllithium; diphenyl phosphoryl azide; ammonium formate; hydrazine hydrate; ethylene glycol; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

Reference yield:

3-(3,5-dibromobenzyl)pyridine (145691-54-9) → ethyl 3-{3-[2-(4-fluorophenylsulphonylamino)ethyl]-5-(pyridin-3-ylmethyl)phenyl}propanoate (145690-73-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / Pd(OAc)2, tri-o-tolylphosphine, Et₃N / acetonitrile / 1 h / Heating

2: 95 percent / HCO₂NH₄ / 10percent Pd/C / ethanol; tetrahydrofuran / 1 h / 60 °C

3: 43 percent / aq. NaOH / ethanol / 0.75 h / Heating

4: diphenyl phosphorazidate, Et₃N / 18 h / Heating

5: TFA / CH₂Cl₂ / 4 h / Ambient temperature

6: Et₃N / CH₂Cl₂ / 2.5 h / Ambient temperature

With palladium diacetate; sodium hydroxide; diphenyl phosphoryl azide; ammonium formate; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

upstream raw materials:

4-Fluorobenzenesulfonyl chloride

ethyl 3-[3-(2-aminoethyl)-5-(pyridin-3-ylmethyl)phenyl]propanoate

pyridine-3-carbonitrile

1,3,5-trisbromobenzene

Refernces

• 1、 -. "Pyridine derived agents for cardiovascular diseases". . . Retrieved 2008/06/13.