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

Base Information

• Chemical Name: N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide
• CAS No.: 1257830-24-2
• Molecular Formula: C₂₆H₂₇N₃O₄S
• Molecular Weight: 477.584

Synonyms:N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide

Chemical Property of N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide

Chemical Property:

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Technology Process of N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide

There total 6 articles about N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-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: 21.0%

3-(3-bromo-6-tert-butyl-5-methoxy-8-quinolyl)-1H-pyridin-2-one (1257830-28-6) + 4-(methylsulfonylamino)phenyl boronic acid (380430-57-9) → N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide (1257830-24-2)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; at 115 ℃; for 1h; microwave irradiation; sealed tube;

Reference yield:

4-(1,1-dimethylethyl)-3-(methoxy)benzoic acid (79822-46-1) → N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide (1257830-24-2)

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: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; dichloromethane / 1 h / 115 °C / Inert atmosphere; Sealed tube; Microwave irradiation

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

5.2: 2 h / 100 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; dichloromethane / 1 h / 115 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenylphosphoranyl azide; water; bromine; sodium carbonate; acetic acid; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: |Curtius Rearrangement;

DOI:10.1021/jm401329s

Reference yield:

ethyl N-(4-tert-butyl-3-methoxyphenyl)carbamate (1485748-67-1) → N-[4-[6-tert-butyl-5-methoxy-8-(2-oxo-1H-pyridin-3-yl)-3-quinolyl]phenyl]methanesulfonamide (1257830-24-2)

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: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; dichloromethane / 1 h / 115 °C / Inert atmosphere; Sealed tube; Microwave irradiation

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

4.2: 2 h / 100 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; dichloromethane / 1 h / 115 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; bromine; sodium carbonate; acetic acid; potassium hydroxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm401329s

upstream raw materials:

3-(3-bromo-6-tert-butyl-5-methoxy-8-quinolyl)-1H-pyridin-2-one

4-(methylsulfonylamino)phenyl boronic acid

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

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

Downstream raw materials:

N-{4-[6-tert-butyl-8-(5-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-5-methoxy-quinolin-3-yl]-phenyl}-methanesulfonamide

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