6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

Base Information

• Chemical Name: 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester
• CAS No.: 1265907-54-7
• Molecular Formula: C₂₇H₃₂Cl₂N₂O₆
• Molecular Weight: 551.467
• Mol file: 1265907-54-7.mol

Synonyms:6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

Chemical Property of 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

There total 4 articles about 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl 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: 99.0%

2-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (1206625-60-6) + 1-(1,1-dimethylethyl) 3-ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate (176525-98-7) → 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-54-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; at 50 - 83 ℃; for 1.08333h; Inert atmosphere; Large scale reaction;

DOI:10.1021/jo102070e

Reference yield:

5-bromo-2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]pyridine (945999-98-4) → 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl acetamide / 20 h / 80 - 85 °C / Inert atmosphere; Large scale reaction

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 1.08 h / 50 - 83 °C / Inert atmosphere; Large scale reaction

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; In 1,2-dimethoxyethane; N,N-dimethyl acetamide; water; 2: Suzuki coupling;

DOI:10.1021/jo102070e

Reference yield:

p-cresol (106-44-5) → 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester (1265907-54-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hypochlorite / water; acetonitrile / 0 - 18 °C / Inert atmosphere; Large scale reaction

2.1: 1-methyl-1H-imidazole / N,N-dimethyl acetamide / 2.25 h / 110 °C / Inert atmosphere; Large scale reaction

2.2: 0.5 h / 20 °C / Inert atmosphere; Large scale reaction

2.3: 80 - 90 °C / Inert atmosphere; Large scale reaction

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl acetamide / 20 h / 80 - 85 °C / Inert atmosphere; Large scale reaction

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 1.08 h / 50 - 83 °C / Inert atmosphere; Large scale reaction

With 1-methyl-1H-imidazole; sodium hypochlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium carbonate; In 1,2-dimethoxyethane; N,N-dimethyl acetamide; water; acetonitrile; 4.1: Suzuki coupling;

DOI:10.1021/jo102070e

upstream raw materials:

5-bromo-2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]pyridine

2-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

1-(1,1-dimethylethyl) 3-ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

p-cresol

Downstream raw materials:

MK-1597

(3'R,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)benzyl]cyclopropylamide acetate

(3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester

C₂₇H₃₄Cl₂N₂O₆