methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate

Base Information

• Chemical Name: methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate
• CAS No.: 877272-24-7
• Molecular Formula: C₂₃H₂₅BrN₂O₃
• Molecular Weight: 457.367
• Mol file: 877272-24-7.mol

Synonyms:methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate

Chemical Property of methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate

There total 4 articles about methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate 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: 58.0%

2-bromo-pyridin-3-ol (6602-32-0) + methyl 3-cyclohexyl-1-(2-hydroxyethyl)-1H-indole-6-carboxylate (877272-19-0) → methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate (877272-24-7)

Guidance literature:

2-bromo-pyridin-3-ol; With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

methyl 3-cyclohexyl-1-(2-hydroxyethyl)-1H-indole-6-carboxylate; In tetrahydrofuran; at 20 ℃; for 18h;

Reference yield:

methyl 3-cyclohexyl-1H-indole-6-carboxylate (494799-18-7) → methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate (877272-24-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C

1.2: 2 h / 20 °C

2.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / water; ethyl acetate / 72 h / 20 °C

3.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C

3.2: 20 °C

With hydrogenchloride; di-tert-butyl-diazodicarboxylate; palladium 10% on activated carbon; hydrogen; sodium hydride; triphenylphosphine; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil; 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction;

DOI:10.1039/c1ob05525a

Reference yield:

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8) → methyl 1-(2-(2-bromopyridin-3-yloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate (877272-24-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium acetate / acetonitrile / 150 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C

2.2: 2 h / 20 °C

3.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / water; ethyl acetate / 72 h / 20 °C

4.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C

4.2: 20 °C

With hydrogenchloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; di-tert-butyl-diazodicarboxylate; palladium 10% on activated carbon; hydrogen; sodium acetate; sodium hydride; triphenylphosphine; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; mineral oil; 4.1: Mitsunobu reaction / 4.2: Mitsunobu reaction;

DOI:10.1039/c1ob05525a

upstream raw materials:

2-bromo-pyridin-3-ol

methyl 3-cyclohexyl-1-(2-hydroxyethyl)-1H-indole-6-carboxylate

methyl 3-cyclohexyl-1H-indole-6-carboxylate

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate