6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Base Information

• Chemical Name: 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid
• CAS No.: 1415899-33-0
• Molecular Formula: C₁₅H₁₁ClF₂N₂O₂
• Molecular Weight: 324.714
• Mol file: 1415899-33-0.mol

Synonyms:6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Chemical Property of 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

There total 4 articles about 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid 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:

methyl 5-bromopicolinate (29682-15-3) → 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1415899-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 h / 60 °C

1.2: 2 h / 0 - 95 °C

2.1: caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 110 °C / Inert atmosphere

3.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide; water / 48 h / 100 °C

3.2: pH 3 / Acidic conditions

With caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 3-chloro-benzenecarboperoxoic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

6-chloro-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid methyl ester (1415898-87-1) + 3-chlorophenylboronic acid (63503-60-6) → 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1415899-33-0)

Guidance literature:

6-chloro-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid methyl ester; 3-chlorophenylboronic acid; With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; N,N-dimethyl-formamide; at 100 ℃; for 48h;

In water; N,N-dimethyl-formamide; pH=3; Acidic conditions;

Reference yield:

5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (1214353-79-3) → 6-(3-chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (1415899-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 110 °C / Inert atmosphere

2.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide; water / 48 h / 100 °C

2.2: pH 3 / Acidic conditions

With caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

6-chloro-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid methyl ester

3-chlorophenylboronic acid

methyl 5-bromopicolinate

5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester