2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester
• CAS No.: 863579-21-9
• Molecular Formula: C₂₄H₂₆BrNO₂
• Molecular Weight: 440.38
• Mol file: 863579-21-9.mol

Synonyms:2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Chemical Property of 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

There total 5 articles about 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester 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: 72.0%

3-cyclohexyl-2-[2-(2-hydroxyethyl)phenyl]-1H-indole-6-carboxylic acid methyl ester (863579-20-8) → 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester (863579-21-9)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In chloroform; at 20 ℃; for 0.0833333h;

DOI:10.1021/jm0610245

Reference yield:

2-bromophenylethyl alcohol (1074-16-4) → 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester (863579-21-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 81 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 1 h / 20 °C

2.1: triisopropyl borate; n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

2.2: 56 percent / aq. HCl / tetrahydrofuran; hexane

3.1: 77 percent / NaHCO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 7 h / Heating

4.1: 67 percent / aq. HCl / methanol; tetrahydrofuran / 2 h / 20 °C

5.1: 72 percent / CBr₄; PPh₃ / CHCl₃ / 0.08 h / 20 °C

With hydrogenchloride; n-butyllithium; Triisopropyl borate; carbon tetrabromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; chloroform; water; 3.1: Suzuki coupling;

DOI:10.1021/jm0610245

Reference yield:

2-(2-bromophenyl)ethyl tetrahydro-2H-pyran-2-yl ether (143888-88-4) → 2-[2-(2-bromoethyl)phenyl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester (863579-21-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triisopropyl borate; n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

1.2: 56 percent / aq. HCl / tetrahydrofuran; hexane

2.1: 77 percent / NaHCO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 7 h / Heating

3.1: 67 percent / aq. HCl / methanol; tetrahydrofuran / 2 h / 20 °C

4.1: 72 percent / CBr₄; PPh₃ / CHCl₃ / 0.08 h / 20 °C

With hydrogenchloride; n-butyllithium; Triisopropyl borate; carbon tetrabromide; sodium hydrogencarbonate; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; chloroform; water; 2.1: Suzuki coupling;

DOI:10.1021/jm0610245

upstream raw materials:

3-cyclohexyl-2-[2-(2-hydroxyethyl)phenyl]-1H-indole-6-carboxylic acid methyl ester

3-cyclohexyl-2-{2-[2-(tetrahydropyran-2-yloxy)ethyl]phenyl}-1H-indole-6-carboxylic acid methyl ester

2-bromophenylethyl alcohol

2-(2-bromophenyl)ethyl tetrahydro-2H-pyran-2-yl ether