3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

Base Information

• Chemical Name: 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester
• CAS No.: 445490-68-6
• Molecular Formula: C₂₉H₂₆N₂O₆
• Molecular Weight: 498.535
• Mol file: 445490-68-6.mol

Synonyms:3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

Chemical Property of 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

There total 6 articles about 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic 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: 96.0%

3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester (445490-67-5) + N-hydroxyphthalimide (524-38-9) + diisopropyl (E)-azodicarboxylate (2446-83-5) → 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester (445490-68-6)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran;

Reference yield: 96.0%

3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester (445490-67-5) + N-hydroxyphthalimide (524-38-9) → 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester (445490-68-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.01.028

Reference yield:

2-methyl-1-nitro-4-[2-(phenylmethoxy)ethoxy]benzene (193358-15-5) → 3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester (445490-68-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyrrolidine / dimethylformamide / 16 h / 120 °C

1.2: 22 percent / H₂ / Pd/C / ethyl acetate; methanol

2.1: 69 percent / TBAF / 1,2-dimethoxy-ethane / 16 °C

3.1: 80 percent / H₂ / Pd/C / ethyl acetate; methanol

4.1: 96 percent / PPh₃; DIAD / tetrahydrofuran

With pyrrolidine; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Michael addition / 4.1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2005.01.028

upstream raw materials:

3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester

N-hydroxyphthalimide

2-methyl-1-nitro-4-[2-(phenylmethoxy)ethoxy]benzene

5-(2-benzyloxyethoxy)-1H-indole

Downstream raw materials:

3-(5-{2-[N-(4,5-Dihydro-1H-imidazol-2-yl)-aminooxy]-ethoxy}-indol-1-yl)-3-phenyl-propionic acid ethyl ester

3-[5-(2-aminooxy-ethoxy)-indol-1yl]-3-phenyl-propionic acid ethyl ester