N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Base Information

• Chemical Name: N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide
• CAS No.: 1485749-47-0
• Molecular Formula: C₂₇H₃₀N₄O₅S
• Molecular Weight: 522.625

Synonyms:N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Chemical Property of N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

There total 6 articles about N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide 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: 47.0%

2,4‐dimethoxy‐5‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)pyrimidine (936250-17-8) + N-[4-(8-bromo-6-tert-butyl-5-methoxy-3-quinolyl)phenyl]methanesulfonamide (1257830-36-6) → N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide (1485749-47-0)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; In 1,4-dioxane; water; at 100 ℃; for 0.5h; Inert atmosphere; Sealed tube;

DOI:10.1021/jm401329s

Reference yield:

ethyl N-(4-tert-butyl-3-methoxyphenyl)carbamate (1485748-67-1) → N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide (1485749-47-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hydroxide; water / ethanol / 15 h / Reflux; Inert atmosphere

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

3.1: bromine; acetic acid / 0.25 h / 20 °C / Inert atmosphere

3.2: 4 h / 100 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; toluene / 1 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation

5.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 0.5 h / 100 °C / Inert atmosphere; Sealed tube

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; water; bromine; sodium carbonate; caesium carbonate; acetic acid; potassium hydroxide; In 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm401329s

Reference yield:

4-(1,1-dimethylethyl)-3-(methoxy)benzoic acid (79822-46-1) → N-[4-[6-tert-butyl-8-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide (1485749-47-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diphenylphosphoranyl azide; triethylamine / tetrahydrofuran / 23 h / Reflux; Inert atmosphere

2.1: potassium hydroxide; water / ethanol / 15 h / Reflux; Inert atmosphere

3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

4.1: bromine; acetic acid / 0.25 h / 20 °C / Inert atmosphere

4.2: 4 h / 100 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; toluene / 1 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation

6.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 0.5 h / 100 °C / Inert atmosphere; Sealed tube

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; diphenylphosphoranyl azide; water; bromine; sodium carbonate; caesium carbonate; acetic acid; triethylamine; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; toluene; 1.1: |Curtius Rearrangement;

DOI:10.1021/jm401329s

upstream raw materials:

2,4‐dimethoxy‐5‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)pyrimidine

N-[4-(8-bromo-6-tert-butyl-5-methoxy-3-quinolyl)phenyl]methanesulfonamide

4-(1,1-dimethylethyl)-3-(methoxy)benzoic acid

ethyl N-(4-tert-butyl-3-methoxyphenyl)carbamate

Downstream raw materials:

N-[4-[6-tert-butyl-5-methoxy-8-(4-methoxy-1-methyl-2-oxo-pyrimidin-5-yl)-3-quinolyl]phenyl]methanesulfonamide

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