2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester
• CAS No.: 863578-48-7
• Molecular Formula: C₃₃H₄₃NO₈
• Molecular Weight: 581.706
• Mol file: 863578-48-7.mol

Synonyms:2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester

Chemical Property of 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester

There total 5 articles about 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-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:

methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (494799-19-8) → 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester (863578-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / LiCl; Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 22 h / 90 °C

2.1: NaH / dimethylformamide / 0.33 h / 20 °C

2.2: dimethylformamide / 4 h / 20 °C

With sodium hydride; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 1.1: Suzuki coupling;

DOI:10.1021/jm0610245

Reference yield:

2,4-bis(methoxymethoxy)phenylboronic acid (863578-46-5) → 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester (863578-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / LiCl; Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 22 h / 90 °C

2.1: NaH / dimethylformamide / 0.33 h / 20 °C

2.2: dimethylformamide / 4 h / 20 °C

With sodium hydride; sodium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 1.1: Suzuki coupling;

DOI:10.1021/jm0610245

Reference yield:

4-Bromoresorcinol (6626-15-9) → 2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indole-6-carboxylic acid methyl ester (863578-48-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: K₂CO₃ / acetone / 22 h / 20 °C

2.1: triisopropyl borate; n-BuLi / hexane; tetrahydrofuran / 5 h / -78 °C

2.2: 13.60 g / aq. HCl / tetrahydrofuran; hexane / 0.25 h

3.1: 86 percent / LiCl; Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 22 h / 90 °C

4.1: NaH / dimethylformamide / 0.33 h / 20 °C

4.2: dimethylformamide / 4 h / 20 °C

With n-butyllithium; Triisopropyl borate; sodium hydride; sodium carbonate; potassium carbonate; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water; N,N-dimethyl-formamide; acetone; 3.1: Suzuki coupling;

DOI:10.1021/jm0610245

upstream raw materials:

2-(2-bromoethoxy)tetrahydropyran

2-(2,4-bismethoxymethoxyphenyl)-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

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

2,4-bis(methoxymethoxy)phenylboronic acid

Downstream raw materials:

3-cyclohexyl-2-(2,4-dihydroxyphenyl)-1-(2-hydroxyethyl)-1H-indole-6-carboxylic acid methyl ester