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

Base Information

• Chemical Name: ethyl cis-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate
• CAS No.: 1438249-48-9
• Molecular Formula: C₁₄H₁₈BrNO₃
• Molecular Weight: 328.206
• Mol file: 1438249-48-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about ethyl cis-4-[(5-bromopyridin-2-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: 10.0%

5-bromopyridin-2-ol (13466-38-1) + 4-hydroxycyclohexyl carboxylic acid ethyl ester (3618-04-0,75877-66-6,17159-80-7) → ethyl trans-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate (1438249-47-8) + ethyl cis-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate (1438249-48-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 - 55 ℃; for 40h; Inert atmosphere;

DOI:10.1021/ml400168h

Reference yield: 74.0%

ethyl cis-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate (1438249-48-9) + bis(pinacol)diborane (73183-34-3) → ethyl cis-4-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclohexanecarboxylate (1438249-50-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

DOI:10.1021/ml400168h

Reference yield:

ethyl cis-4-[(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate (1438249-48-9) → cis-4-{[5-(1H-benzimidazol-2-yl)-2,3'-bipyridin-6'-yl]oxy}cyclohexanecarboxylic acid (1438246-42-4)

Guidance literature:

Multi-step reaction with 4 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

3: potassium peroxymonosulfate / N,N-dimethyl-formamide; water / 20 °C

4: lithium hydroxide / tetrahydrofuran; water; ethanol / 3 h / 60 °C

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

DOI:10.1021/ml400168h

upstream raw materials:

5-bromopyridin-2-ol

4-hydroxycyclohexyl carboxylic acid ethyl ester

Downstream raw materials:

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

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

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

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