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

Base Information

• Chemical Name: 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
• CAS No.: 444663-63-2
• Molecular Formula: C₃₁H₂₈Cl₃FN₂O₃
• Molecular Weight: 601.932
• Mol file: 444663-63-2.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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:

1-tert-butyloxycarbonyl-4-trimethylstannyl-1,2,5,6-tetrahydropyridine (162046-38-0) + 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) → 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 (444663-63-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; In 1,4-dioxane; at 100 ℃;

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

Reference yield:

2,6-dibromo-4-methoxytoluene (14542-71-3) → 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 (444663-63-2)

Guidance literature:

Multi-step reaction with 10 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

10: LiCl; Pd(PPh₃)4 / dioxane / 100 °C

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 chloride; lithium hexamethyldisilazane; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Ullmann cyclization / 7: Suzuki coupling / 10: Stille coupling;

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

Reference yield:

1,3-dibromo-2-(bromomethyl)-5-methoxybenzene (130445-13-5) → 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 (444663-63-2)

Guidance literature:

Multi-step reaction with 9 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

9: LiCl; Pd(PPh₃)4 / dioxane / 100 °C

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 chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Ullmann cyclization / 6: Suzuki coupling / 9: Stille coupling;

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

upstream raw materials:

1-tert-butyloxycarbonyl-4-trimethylstannyl-1,2,5,6-tetrahydropyridine

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

2,6-dibromo-4-methoxytoluene

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

Downstream raw materials:

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