benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate

Base Information

• Chemical Name: benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate
• CAS No.: 1438249-52-5
• Molecular Formula: C₂₃H₂₈BNO₅
• Molecular Weight: 409.29
• Mol file: 1438249-52-5.mol

Synonyms:benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate

Chemical Property of benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate

There total 6 articles about benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate 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:

benzyl 3-[(5-bromopyridin-2-yl)oxy]cyclobutanecarboxylate (1438249-51-4) + bis(pinacol)diborane (73183-34-3) → benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate (1438249-52-5)

Guidance literature:

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

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate (1438249-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 1 h / 0 °C

2: sodium tetrahydroborate; methanol / 1 h / 0 - 20 °C

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 55 °C / Inert atmosphere

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

With methanol; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; di-isopropyl azodicarboxylate; potassium acetate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

Reference yield:

3-oxocyclobutanecarboxylic acid (23761-23-1) → benzyl 3-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}cyclobutanecarboxylate (1438249-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; dmap / dichloromethane / 1 h / 0 °C

2: sodium tetrahydroborate; methanol / 1 h / 0 - 20 °C

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 55 °C / Inert atmosphere

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

With methanol; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; di-isopropyl azodicarboxylate; potassium acetate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

upstream raw materials:

3-oxocyclobutanecarboxylic acid

benzyl chloroformate

benzyl 3-oxocyclobutane-1-carboxylate

5-bromopyridin-2-ol

Downstream raw materials:

benzyl 3-({5-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]-2,3'-bipyridin-6'-yl}oxy)cyclobutanecarboxylate

Refernces