benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate

Base Information

• Chemical Name: benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate
• CAS No.: 1393534-93-4
• Molecular Formula: C₃₂H₂₆N₂O₄
• Molecular Weight: 502.569
• Mol file: 1393534-93-4.mol

Synonyms:

Chemical Property of benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate

There total 3 articles about benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate 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: 45.0%

benzyl 2-(3-(benzyloxy)-5-bromopicolinamido)acetate (1393534-90-1) + naphthalene-2-boronic acid (32316-92-0) → benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate (1393534-93-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine; In tetrahydrofuran; for 40h; Reflux;

DOI:10.1002/anie.201202000

Reference yield:

3-(benzyloxy)-5-bromopicolinic acid (1393534-89-8) → benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate (1393534-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / Inert atmosphere

1.2: 72 h / Inert atmosphere

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine / tetrahydrofuran / 40 h / Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2.1: Suzuki coupling;

DOI:10.1002/anie.201202000

Reference yield:

5-bromo-3-nitropyridine-2-carbonitrile (573675-25-9) → benzyl 2-(3-(benzyloxy)-5-(naphthalen-2-yl)picolinamido)acetate (1393534-93-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 35 °C

1.2: 1.33 h / 20 °C

2.1: water; sodium hydroxide / methanol / Reflux

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / Inert atmosphere

3.2: 72 h / Inert atmosphere

4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine / tetrahydrofuran / 40 h / Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium hydride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 4.1: Suzuki coupling;

DOI:10.1002/anie.201202000

upstream raw materials:

3-(benzyloxy)-5-bromopicolinic acid

benzyl 2-(3-(benzyloxy)-5-bromopicolinamido)acetate

naphthalene-2-boronic acid

5-bromo-3-nitropyridine-2-carbonitrile