6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one

Base Information

• Chemical Name: 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one
• CAS No.: 1354745-77-9
• Molecular Formula: C₂₃H₁₇ClFNO₃
• Molecular Weight: 409.844
• Mol file: 1354745-77-9.mol

Synonyms:6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one

Chemical Property of 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one

There total 9 articles about 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one 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: 92.0%

6-chloro-4-ethoxy-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinoline (1599467-74-9) → 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one (1354745-77-9)

Guidance literature:

With hydrogen bromide; acetic acid; In water; at 90 ℃; for 24h;

DOI:10.1021/jm500147k

Reference yield:

C13H16ClNO3 → 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one (1354745-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dowtherm A / 0.33 h / 250 °C

2.1: iodine; potassium iodide; N-butylamine / water; N,N-dimethyl-formamide / 12 h / 20 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C

3.2: 8 h / 50 °C

4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 18 h / 85 °C

5.1: acetic acid; hydrogen bromide / water / 24 h / 90 °C

With dowtherm A; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; iodine; potassium carbonate; acetic acid; N-butylamine; potassium iodide; In water; N,N-dimethyl-formamide; 4.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm500147k

Reference yield:

4-bromo-phenol (106-41-2) → 6-chloro-3-(4-(4-fluorophenoxy)phenyl)-7-methoxy-2-methylquinolin-4(1H)-one (1354745-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: copper diacetate; N-ethyl-N,N-diisopropylamine; pyridine / dichloromethane / 12 h / 20 °C / Molecular sieve

2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / N,N-dimethyl-formamide / 18 h / 80 °C / Molecular sieve

3: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 18 h / 85 °C

4: acetic acid; hydrogen bromide / water / 24 h / 90 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; hydrogen bromide; potassium acetate; copper diacetate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; N,N-dimethyl-formamide; 3: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm500147k

upstream raw materials:

4-bromo-phenol

6-chloro-7-methoxy-2-methylquinolin-4(1H)-one

6-chloro-3-iodo-7-methoxy-2-methylquinolin-4(1H)-one

2-(4-(4-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane