3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester
• CAS No.: 179106-75-3
• Molecular Formula: C₂₈H₂₃Cl₂NO₇S
• Molecular Weight: 588.465
• Mol file: 179106-75-3.mol

Synonyms:

Chemical Property of 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

There total 5 articles about 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic 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:

(Z)-2-(4-Methoxyphenyl)-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester (179106-71-9) → 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-75-3)

Guidance literature:

With formic acid; at 20 ℃;

DOI:10.1021/jm0491849

Reference yield:

4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-92-4) → 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C

1.2: 53 percent / tetrahydrofuran / 2 h / -78 - 20 °C

2.1: 427 mg / tri-2-furylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; K₂CO₃ / tetrahydrofuran / 216 h / 55 - 60 °C

3.1: 276 mg / aq. HCO₂H / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; trifuran-2-yl-phosphane; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1.2: Horner-Emmons reaction / 2.1: Suzuki-Miyaura reaction;

DOI:10.1021/jm0491849

Reference yield:

(Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-70-8) → 3-[2-carboxy-2-(4-methoxy-phenyl)-vinyl]-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 427 mg / tri-2-furylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; K₂CO₃ / tetrahydrofuran / 216 h / 55 - 60 °C

2: 276 mg / aq. HCO₂H / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; trifuran-2-yl-phosphane; potassium carbonate; In tetrahydrofuran; 1: Suzuki-Miyaura reaction;

DOI:10.1021/jm0491849

upstream raw materials:

(Z)-2-(4-Methoxyphenyl)-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester

4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

(Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

4,6-dichloro-indole-2-carboxylic acid,ethyl ester