1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1Z)-3-(1,1-dimethylethoxy)-3-oxo-2-(2-thienyl)-1-propen yl]-1-[(4-methylphenyl)sulfonyl]-, ethyl ester

Base Information

• Chemical Name: 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1Z)-3-(1,1-dimethylethoxy)-3-oxo-2-(2-thienyl)-1-propen yl]-1-[(4-methylphenyl)sulfonyl]-, ethyl ester
• CAS No.: 179328-06-4
• Molecular Formula: C29H27Cl2NO6S2
• Molecular Weight: 620.574
• Mol file: 179328-06-4.mol

Synonyms:

Chemical Property of 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1Z)-3-(1,1-dimethylethoxy)-3-oxo-2-(2-thienyl)-1-propen yl]-1-[(4-methylphenyl)sulfonyl]-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1Z)-3-(1,1-dimethylethoxy)-3-oxo-2-(2-thienyl)-1-propen yl]-1-[(4-methylphenyl)sulfonyl]-, ethyl ester

There total 7 articles about 1H-Indole-2-carboxylic acid, 4,6-dichloro-3-[(1Z)-3-(1,1-dimethylethoxy)-3-oxo-2-(2-thienyl)-1-propen yl]-1-[(4-methylphenyl)sulfonyl]-, 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: 88.0%

(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) + thiophene boronic acid (6165-68-0) → 3-(2-tert-butoxycarbonyl-2-thiophen-2-yl-vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179328-06-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; potassium carbonate; In tetrahydrofuran; at 55 - 60 ℃;

DOI:10.1021/jm0491849

Reference yield:

bromo(diethoxyphosphoryl)acetic acid tert-butyl ester (179106-93-5) → 3-(2-tert-butoxycarbonyl-2-thiophen-2-yl-vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179328-06-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.1: 88 percent / tri-2-furylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; K₂CO₃ / tetrahydrofuran / 55 - 60 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 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:

dibromo(diethoxyphosphoryl)acetic acid tert-butyl ester (179106-94-6) → 3-(2-tert-butoxycarbonyl-2-thiophen-2-yl-vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179328-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / aq. SnCl₂ / 2-methyl-propan-2-ol / 0.25 h / cooling

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

2.2: 53 percent / tetrahydrofuran / 2 h / -78 - 20 °C

3.1: 88 percent / tri-2-furylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; K₂CO₃ / tetrahydrofuran / 55 - 60 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; potassium carbonate; tin(ll) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; tert-butyl alcohol; 2.2: Horner-Emmons reaction / 3.1: Suzuki-Miyaura reaction;

DOI:10.1021/jm0491849

upstream raw materials:

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

thiophene boronic acid

bromo(diethoxyphosphoryl)acetic acid tert-butyl ester

dibromo(diethoxyphosphoryl)acetic acid tert-butyl ester

Downstream raw materials:

(Z)-2-(Thien-2-yl)-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid