ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate

Base Information

• Chemical Name: ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate
• CAS No.: 1366132-13-9
• Molecular Formula: C₂₄H₂₀F₂N₄O₅S
• Molecular Weight: 514.509
• Mol file: 1366132-13-9.mol

Synonyms:ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate

Chemical Property of ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate

There total 8 articles about ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate 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: 35.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + N-[5-(2-amino-3-bromo-6-quinolinyl)-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (1366127-99-2) → ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate (1366132-13-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; In dimethyl sulfoxide; at 90 ℃; for 16h; under 4654.46 Torr;

Reference yield:

p-aminoiodobenzene (540-37-4) → ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate (1366132-13-9)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / dichloromethane / 2 h / 20 °C

2: sulfuric acid / 2 h / 0 - 20 °C

3: N-Bromosuccinimide / dichloromethane; N,N-dimethyl-formamide / 22 h / 20 °C

4: trichlorophosphate / 1 h / 100 °C

5: triethylamine / butan-1-ol / 29 h / 135 °C / Sealed tube

6: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 60 °C / Inert atmosphere

7: trifluoroacetic acid / 6 h / 65 °C

8: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / palladium diacetate / dimethyl sulfoxide / 16 h / 90 °C / 4654.46 Torr

With pyridine; N-Bromosuccinimide; sulfuric acid; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; trichlorophosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; butan-1-ol; 6: Suzuki Coupling;

Reference yield:

6-iodoquinolin-2(1H)-one (99455-01-3) → ethyl 2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylate (1366132-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: N-Bromosuccinimide / dichloromethane; N,N-dimethyl-formamide / 22 h / 20 °C

2: trichlorophosphate / 1 h / 100 °C

3: triethylamine / butan-1-ol / 29 h / 135 °C / Sealed tube

4: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 60 °C / Inert atmosphere

5: trifluoroacetic acid / 6 h / 65 °C

6: N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / palladium diacetate / dimethyl sulfoxide / 16 h / 90 °C / 4654.46 Torr

With N-Bromosuccinimide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; trichlorophosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; butan-1-ol; 4: Suzuki Coupling;

upstream raw materials:

ethanol

carbon monoxide

N-[5-(2-amino-3-bromo-6-quinolinyl)-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

p-aminoiodobenzene

Downstream raw materials:

2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)-N-phenylquinoline-3-carboxamide

2-amino-6-(5-{[(2,4-fifluorophenyl)sulfonyl]amino}-6-methoxypyridin-3-yl)quinoline-3-carboxylic acid lithium salt