tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate

Base Information

• Chemical Name: tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate
• CAS No.: 142535-29-3
• Molecular Formula: C₃₂H₃₉NO₆
• Molecular Weight: 533.665
• Mol file: 142535-29-3.mol

Synonyms:tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate

Chemical Property of tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate

There total 7 articles about tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate 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: 84.0%

tert-butyl 4-<<6-(2-cyclopentylethoxy)-3-formylindol-1-yl>methyl>-3-methoxybenzoate (142535-28-2) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate (142535-29-3)

Guidance literature:

In 1,4-dioxane; for 48h; Heating;

DOI:10.1021/jm00091a010

Reference yield:

4-(benzyloxy)-1-methyl-2-nitrobenzene (24239-67-6) → tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate (142535-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / dimethylformamide / 80 h / 130 °C

2: 39 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 0.5 h

3: 75 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran

4: 1.) POCl₃, 2.) aq. NaOH / 1.) 0 deg C, 30 min, 2.) RT, 1 h, 3.) reflux, 5 min

5: 54 percent / K₂CO₃ / dimethylformamide / 72 h

6: 84 percent / dioxane / 48 h / Heating

With sodium hydroxide; hydrogen; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00091a010

Reference yield:

(E)-5-(benzyloxy)-2-<2-(dimethylamino)vinyl>nitrobenzene (99474-13-2) → tert-butyl (E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoate (142535-29-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 39 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 0.5 h

2: 75 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran

3: 1.) POCl₃, 2.) aq. NaOH / 1.) 0 deg C, 30 min, 2.) RT, 1 h, 3.) reflux, 5 min

4: 54 percent / K₂CO₃ / dimethylformamide / 72 h

5: 84 percent / dioxane / 48 h / Heating

With sodium hydroxide; hydrogen; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00091a010

upstream raw materials:

tert-butyl 4-<<6-(2-cyclopentylethoxy)-3-formylindol-1-yl>methyl>-3-methoxybenzoate

methyl (triphenylphosphoranylidene)acetate

6-hydroxy-1H-indole

2-cyclopentyl-ethanol

Downstream raw materials:

3-[1-(4-Benzenesulfonylaminocarbonyl-2-methoxy-benzyl)-6-(2-cyclopentyl-ethoxy)-1H-indol-3-yl]-propionamide

4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethyl>indol-1-yl>methyl>-3-methoxybenzoic acid

4-<<6-(2-cyclopentylethoxy)-3-(2-carbamoylethyl)indol-1-yl>methyl>-3-methoxybenzoic acid

(E)-4-<<6-(2-cyclopentylethoxy)-3-<2-(methoxycarbonyl)ethylidenyl>indol-1-yl>methyl>-3-methoxybenzoic acid

Refernces