6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid

Base Information

• Chemical Name: 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid
• CAS No.: 1093631-52-7
• Molecular Formula: C₂₈H₂₁Cl₂NO₄S
• Molecular Weight: 538.451
• Mol file: 1093631-52-7.mol

Synonyms:

Chemical Property of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid

There total 9 articles about 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic 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:

6-methoxy-benzo[b]thiophene (90560-10-4) → 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid (1093631-52-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aluminum (III) chloride / dichloromethane / 1.25 h / -75 - -40 °C / Inert atmosphere

1.2: 1.5 h / -40 - 0 °C

2.1: water; potassium hydroxide / tetrahydrofuran / 20 °C / Cooling

2.2: pH 3

3.1: thionyl chloride / 4 h / Inert atmosphere; Reflux

4.1: boron tribromide / dichloromethane / 1 h / Inert atmosphere; Cooling with ice

4.2: Cooling

5.1: pyridine / dichloromethane / 0.08 h / Inert atmosphere; Cooling with ice

5.2: 4 h / Cooling with ice

6.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 3 h / 80 °C / Inert atmosphere

7.1: di-isopropyl azodicarboxylate / dichloromethane / 20 °C / Inert atmosphere

8.1: lithium hydroxide / 1,4-dioxane / 4 h / 20 °C / Inert atmosphere

8.2: 23.5 h

With pyridine; aluminum (III) chloride; thionyl chloride; di-isopropyl azodicarboxylate; water; boron tribromide; sodium carbonate; potassium hydroxide; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; 6.1: Suzuki Coupling / 7.1: Mitsunobu reaction;

Reference yield:

3-methoxybenzenethiol (15570-12-4) → 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid (1093631-52-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / acetone

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 72 h / 20 °C

3.1: aluminum (III) chloride / dichloromethane / 1.25 h / -75 - -40 °C / Inert atmosphere

3.2: 1.5 h / -40 - 0 °C

4.1: water; potassium hydroxide / tetrahydrofuran / 20 °C / Cooling

4.2: pH 3

5.1: thionyl chloride / 4 h / Inert atmosphere; Reflux

6.1: boron tribromide / dichloromethane / 1 h / Inert atmosphere; Cooling with ice

6.2: Cooling

7.1: pyridine / dichloromethane / 0.08 h / Inert atmosphere; Cooling with ice

7.2: 4 h / Cooling with ice

8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 3 h / 80 °C / Inert atmosphere

9.1: di-isopropyl azodicarboxylate / dichloromethane / 20 °C / Inert atmosphere

10.1: lithium hydroxide / 1,4-dioxane / 4 h / 20 °C / Inert atmosphere

10.2: 23.5 h

With pyridine; aluminum (III) chloride; thionyl chloride; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; water; boron tribromide; sodium carbonate; potassium carbonate; potassium hydroxide; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; acetone; 8.1: Suzuki Coupling / 9.1: Mitsunobu reaction;

Reference yield:

6-methoxy-benzo[b]thiophene-3-carboxylic acid (43121-88-6) → 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-benzothiophene-3-carboxylic acid (1093631-52-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 4 h / Inert atmosphere; Reflux

2.1: boron tribromide / dichloromethane / 1 h / Inert atmosphere; Cooling with ice

2.2: Cooling

3.1: pyridine / dichloromethane / 0.08 h / Inert atmosphere; Cooling with ice

3.2: 4 h / Cooling with ice

4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 3 h / 80 °C / Inert atmosphere

5.1: di-isopropyl azodicarboxylate / dichloromethane / 20 °C / Inert atmosphere

6.1: lithium hydroxide / 1,4-dioxane / 4 h / 20 °C / Inert atmosphere

6.2: 23.5 h

With pyridine; thionyl chloride; di-isopropyl azodicarboxylate; boron tribromide; sodium carbonate; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; 4.1: Suzuki Coupling / 5.1: Mitsunobu reaction;

upstream raw materials:

6-methoxy-benzo[b]thiophene

3-methoxybenzenethiol

6-methoxy-benzo[b]thiophene-3-carboxylic acid

1-[(2,2-diethoxyethyl)sulfanyl]-3-methoxybenzene