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

Base Information

• Chemical Name: (Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester
• CAS No.: 179106-70-8
• Molecular Formula: C₂₅H₂₄BrCl₂NO₆S
• Molecular Weight: 617.345
• Mol file: 179106-70-8.mol

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

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

There total 6 articles about (Z)-3-(2-bromo-2-(tert-butoxycarbonyl)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: 53.0%

bromo(diethoxyphosphoryl)acetic acid tert-butyl ester (179106-93-5) + 4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (179106-92-4) → (E)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-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 (179106-70-8)

Guidance literature:

bromo(diethoxyphosphoryl)acetic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.166667h;

4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester; In tetrahydrofuran; at -78 - 20 ℃; for 2h;

DOI:10.1021/jm0491849

Reference yield:

dibromo(diethoxyphosphoryl)acetic acid tert-butyl ester (179106-94-6) → (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)

Guidance literature:

Multi-step reaction with 2 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

With tin(ll) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; tert-butyl alcohol; 2.2: Horner-Emmons reaction;

DOI:10.1021/jm0491849

Reference yield:

4,6-dichloro-indole-2-carboxylic acid,ethyl ester (53995-82-7) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 64.7 percent / POCl₃ / CH₂Cl₂ / 2.5 h / Heating

2.1: 84 percent / K₂CO₃ / dimethylformamide / 0.5 h / 20 °C

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

3.2: 53 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With potassium carbonate; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.2: Horner-Emmons reaction;

DOI:10.1021/jm0491849

upstream raw materials:

bromo(diethoxyphosphoryl)acetic acid tert-butyl ester

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

dibromo(diethoxyphosphoryl)acetic acid tert-butyl ester

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

Downstream raw materials:

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

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

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

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