N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide

Base Information

• Chemical Name: N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide
• CAS No.: 1126368-33-9
• Molecular Formula: C₂₃H₁₉ClN₄O₂
• Molecular Weight: 418.882
• Mol file: 1126368-33-9.mol

Synonyms:N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide

Chemical Property of N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide

There total 10 articles about N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide 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: 9.0%

2-bromo-1H-imidazole (16681-56-4,151223-74-4) + N-(4-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(pyridin-2-ylmethoxy)benzamide (1126367-36-9) → N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide (1126368-33-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; water; at 130 ℃; for 2h; Microwave irradiation;

DOI:10.1016/j.bmc.2019.115227

Reference yield:

5-bromo-4-chloro-2-methylaniline (1126367-88-1) → N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide (1126368-33-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; triethylamine / dichloromethane / 2 h / 50 °C

2: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 5 h / 115 °C / Microwave irradiation

3: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 130 °C / Microwave irradiation

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; triethylamine; In 1,4-dioxane; dichloromethane; water; 2: |Suzuki Coupling / 3: |Suzuki Coupling;

DOI:10.1016/j.bmc.2019.115227

Reference yield:

Ethyl 4-hydroxybenzoate (120-47-8) → N-[4-chloro-5-(1H-imidazol-2-yl)-2-methylphenyl]-4-(pyridin-2-ylmethoxy)benzamide (1126368-33-9)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / N,N-dimethyl acetamide

2: sodium hydroxide / ethanol

3: thionyl chloride / 1 h / 18 - 30 °C

4: pyridine; triethylamine / dichloromethane / 2 h / 50 °C

5: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 5 h / 115 °C / Microwave irradiation

6: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 130 °C / Microwave irradiation

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; potassium acetate; potassium carbonate; triethylamine; sodium hydroxide; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl acetamide; water; 5: |Suzuki Coupling / 6: |Suzuki Coupling;

DOI:10.1016/j.bmc.2019.115227

upstream raw materials:

5-bromo-4-chloro-2-methylaniline

Ethyl 4-hydroxybenzoate

2-chloromethylpyridine hydrochloride

N-(5-bromo-4-chloro-2-methylphenyl)-4-(pyridin-2-ylmethoxy)benzamide