N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

Base Information

• Chemical Name: N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide
• CAS No.: 1534370-75-6
• Molecular Formula: C₂₃H₁₈F₃N₃O₃
• Molecular Weight: 441.409

Synonyms:N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

Chemical Property of N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

There total 6 articles about N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide 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: 62.0%

N-methyl-2-[2-oxo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide (1534370-71-2) + 3-bromo-2-picoline (38749-79-0) → N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide (1534370-75-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 2h; Reflux; Inert atmosphere;

DOI:10.1055/s-0033-1339799

Reference yield:

2-amino-4-bromo-phenol (40925-68-6) → N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide (1534370-75-6)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice; Inert atmosphere

3: hydrogenchloride; acetic acid / 1,4-dioxane / 6.5 h / 50 °C / Inert atmosphere

4: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

5: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 15 h / 20 °C / Inert atmosphere; Reflux

6: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 20 °C / Reflux; Inert atmosphere

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; acetic acid; triethylamine; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0033-1339799

Reference yield:

4-bromo-2-nitrophenol (7693-52-9) → N-methyl-2-[5-(2-methylpyridin-3-yl)-2-oxo-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide (1534370-75-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 5% rhodium-on-charcoal; hydrogen / tetrahydrofuran / 11 h / 20 °C / Inert atmosphere

2: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice; Inert atmosphere

4: hydrogenchloride; acetic acid / 1,4-dioxane / 6.5 h / 50 °C / Inert atmosphere

5: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

6: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 15 h / 20 °C / Inert atmosphere; Reflux

7: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 20 °C / Reflux; Inert atmosphere

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 5% rhodium-on-charcoal; hydrogen; potassium acetate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; acetic acid; triethylamine; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0033-1339799

upstream raw materials:

N-methyl-2-[2-oxo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazol-3(2H)-yl]-N-[4-(trifluoromethyl)phenyl]acetamide

3-bromo-2-picoline

4-bromo-2-nitrophenol

2-amino-4-bromo-phenol

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