4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester

Base Information

• Chemical Name: 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester
• CAS No.: 1315468-83-7
• Molecular Formula: C₂₇H₂₄ClN₃O₆
• Molecular Weight: 521.957
• Mol file: 1315468-83-7.mol

Synonyms:4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester

Chemical Property of 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester

There total 10 articles about 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl 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: 43.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + [4-(2,5-dichloro-4-bromophenoxy)pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)methanone (1315468-79-1) → 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester (1315468-81-5) + 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester (1315468-83-7)

Guidance literature:

With triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In ethyl acetate; at 120 ℃; for 20h; under 52505.3 Torr;

Reference yield:

ortho-nitrofluorobenzene (1493-27-2,127723-77-7) → 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester (1315468-81-5) + 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester (1315468-83-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 19 h / 20 - 30 °C

2: triethylamine / dichloromethane / 72 h / 20 °C

3: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 20 °C / 900.09 Torr

4: triphenylphosphine / N,N-dimethyl-formamide / 4 h / 135 °C

5: borane-THF / tetrahydrofuran / 20 °C

6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 17 h / 20 °C

7: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / ethyl acetate / 20 h / 120 °C / 52505.3 Torr

With borane-THF; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

4-bromo-2,5-dichlorophenol (1940-42-7,79151-08-9) → 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester (1315468-81-5) + 4-chloro-5-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-phthalic acid dimethyl ester (1315468-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / tetrakis(actonitrile)copper(I) hexafluorophosphate / o-xylene / 16 h / 120 °C

2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 17 h / 20 °C

3: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / ethyl acetate / 20 h / 120 °C / 52505.3 Torr

With caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tetrakis(actonitrile)copper(I) hexafluorophosphate; In o-xylene; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

methanol

carbon monoxide

[4-(2,5-dichloro-4-bromophenoxy)pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)methanone

ortho-nitrofluorobenzene