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
Hs Code.:

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

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

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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%

: 6602-32-0
2-bromo-pyridin-3-ol

: 877272-19-0
methyl 3-cyclohexyl-1-(2-hydroxyethyl)-1H-indole-6-carboxylate

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

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:

: 494799-18-7
methyl 3-cyclohexyl-1H-indole-6-carboxylate

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

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:

: 494799-19-8
methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

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

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