trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester

Base Information

• Chemical Name: trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester
• CAS No.: 444663-62-1
• Molecular Formula: C₂₂H₁₂Cl₃F₄NO₄S
• Molecular Weight: 568.76
• Mol file: 444663-62-1.mol

Synonyms:

Chemical Property of trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester

There total 9 articles about trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester 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:

2,6-dibromo-4-methoxytoluene (14542-71-3) → trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester (444663-62-1)

Guidance literature:

Multi-step reaction with 9 steps

1: NBS; (BzO)2 / CCl₄

2: LHMDS / tetrahydrofuran / -78 °C

3: TFA

4: (COBr)2; DMF / CH₂Cl₂ / -78 - 20 °C

5: DIPEA / CH₂Cl₂

6: 86 percent / CuI; K₂CO₃ / dimethylformamide / 155 °C

7: Na₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 100 °C

8: BBr₃ / CH₂Cl₂

9: iPr₂NEt / CH₂Cl₂

With N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Oxalyl bromide; boron tribromide; sodium carbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium hexamethyldisilazane; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Ullmann cyclization / 7: Suzuki coupling;

DOI:10.1016/S0960-894X(02)00990-3

Reference yield:

1,3-dibromo-2-(bromomethyl)-5-methoxybenzene (130445-13-5) → trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester (444663-62-1)

Guidance literature:

Multi-step reaction with 8 steps

1: LHMDS / tetrahydrofuran / -78 °C

2: TFA

3: (COBr)2; DMF / CH₂Cl₂ / -78 - 20 °C

4: DIPEA / CH₂Cl₂

5: 86 percent / CuI; K₂CO₃ / dimethylformamide / 155 °C

6: Na₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 100 °C

7: BBr₃ / CH₂Cl₂

8: iPr₂NEt / CH₂Cl₂

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Oxalyl bromide; boron tribromide; sodium carbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Ullmann cyclization / 6: Suzuki coupling;

DOI:10.1016/S0960-894X(02)00990-3

Reference yield:

3-(2,6-dibromo-4-methoxy-phenyl)-propionyl bromide → trifluoro-methanesulfonic acid 5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl ester (444663-62-1)

Guidance literature:

Multi-step reaction with 5 steps

1: DIPEA / CH₂Cl₂

2: 86 percent / CuI; K₂CO₃ / dimethylformamide / 155 °C

3: Na₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 100 °C

4: BBr₃ / CH₂Cl₂

5: iPr₂NEt / CH₂Cl₂

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron tribromide; sodium carbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Ullmann cyclization / 3: Suzuki coupling;

DOI:10.1016/S0960-894X(02)00990-3

upstream raw materials:

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

5-(2-chloro-4-fluoro-phenyl)-1-(2,6-dichloro-phenyl)-7-hydroxy-3,4-dihydro-1H-quinolin-2-one

2,6-dibromo-4-methoxytoluene

1,3-dibromo-2-(bromomethyl)-5-methoxybenzene

Downstream raw materials:

7-(1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-2(1H)-quinolinone

5-(2-Chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-(4-piperidinyl)-2(1H)-quinolinone