4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid

Base Information

• Chemical Name: 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid
• CAS No.: 1232861-60-7
• Molecular Formula: C₃₅H₃₂F₅NO₅
• Molecular Weight: 641.635
• Mol file: 1232861-60-7.mol

Synonyms:

Chemical Property of 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid

There total 9 articles about 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid 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:

C39H40F5NO5 → 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid (1232861-60-7)

Guidance literature:

With water; sodium hydroxide; In 1,2-dimethoxyethane; ethanol; at 20 - 50 ℃; for 5h;

DOI:10.1021/acs.jmedchem.5b00741

Reference yield:

1-(2-bromo-5-fluorophenyl)hydrazine hydrochloride (60481-35-8) → 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid (1232861-60-7)

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid / 1.5 h / 100 °C

2: caesium carbonate / N,N-dimethyl-formamide / 1 h / 55 °C

3: diisopropylamine; (Bis(tri-tert-butylphosphine)palladium⁽⁰⁾) / hexane; acetonitrile / 3 h / 20 °C / Inert atmosphere

4: potassium carbonate / ethanol; 1,2-dimethoxyethane / 17 h / 20 °C / Inert atmosphere

5: triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine / dichloromethane / 15 h / 20 °C

6: sodium hydroxide; water / ethanol; 1,2-dimethoxyethane / 5 h / 20 - 50 °C

With sulfuric acid; (Bis(tri-tert-butylphosphine)palladium⁽⁰⁾); water; potassium carbonate; caesium carbonate; diisopropylamine; triphenylphosphine; sodium hydroxide; 1,1'-azodicarbonyl-dipiperidine; In 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: |Fischer Indole Synthesis / 3: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.5b00741

Reference yield:

ethyl 4-(7-bromo-4-fluoro-2-methyl-1H-indol-3-yl)butanoate → 4,4′-[4-fluoro-2-methyl-7-({4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl}ethynyl)-1H-indole-1,3-diyl]dibutanoic acid (1232861-60-7)

Guidance literature:

Multi-step reaction with 5 steps

1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 55 °C

2: diisopropylamine; (Bis(tri-tert-butylphosphine)palladium⁽⁰⁾) / hexane; acetonitrile / 3 h / 20 °C / Inert atmosphere

3: potassium carbonate / ethanol; 1,2-dimethoxyethane / 17 h / 20 °C / Inert atmosphere

4: triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine / dichloromethane / 15 h / 20 °C

5: sodium hydroxide; water / ethanol; 1,2-dimethoxyethane / 5 h / 20 - 50 °C

With (Bis(tri-tert-butylphosphine)palladium⁽⁰⁾); water; potassium carbonate; caesium carbonate; diisopropylamine; triphenylphosphine; sodium hydroxide; 1,1'-azodicarbonyl-dipiperidine; In 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.5b00741

upstream raw materials:

1-(2-bromo-5-fluorophenyl)hydrazine hydrochloride

6-oxoheptanoic acid

2-bromo-1,3,4,5-tetrafluorobenzene