ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate

Base Information

• Chemical Name: ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate
• CAS No.: 1438251-21-8
• Molecular Formula: C₂₀H₂₂N₂O₄
• Molecular Weight: 354.406
• Mol file: 1438251-21-8.mol

Synonyms:ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate

Chemical Property of ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate

There total 3 articles about ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate 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: 80.0%

ethyl cis-4-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclohexanecarboxylate (1438249-50-3) + 6-bromonicotinaldehyde (149806-06-4) → ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate (1438251-21-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

DOI:10.1021/ml400168h

Reference yield:

4-hydroxycyclohexyl carboxylic acid ethyl ester (3618-04-0,75877-66-6,17159-80-7) → ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate (1438251-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 40 h / 20 - 55 °C / Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide; water / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; di-isopropyl azodicarboxylate; potassium acetate; sodium carbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; 1: |Mitsunobu Displacement / 3: |Suzuki Coupling;

DOI:10.1021/ml400168h

Reference yield:

ethyl cis-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate (1438249-48-9) → ethyl cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylate (1438251-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide; water / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium carbonate; In 1,4-dioxane; water; N,N-dimethyl-formamide; 2: |Suzuki Coupling;

DOI:10.1021/ml400168h

upstream raw materials:

ethyl cis-4-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclohexanecarboxylate

6-bromonicotinaldehyde

4-hydroxycyclohexyl carboxylic acid ethyl ester

ethyl cis-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate

Downstream raw materials:

cis-4-[(5-formyl-2,3'-bipyridin-6'-yl)oxy]cyclohexanecarboxylic acid

cis-4-{[5-(1H-benzimidazol-2-yl)-2,3'-bipyridin-6'-yl]oxy}cyclohexanecarboxylic acid

C₂₄H₂₃N₅O₄

cis-4-{[5-(5-chloro-1H-benzimidazol-2-yl)-2,3'-bipyridin-6'-yl]oxy}cyclohexane-carboxylic acid