ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylMethoxy)-1H-indol-2-yl)-2,2-diMethylpropanoate

Base Information

• Chemical Name: ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylMethoxy)-1H-indol-2-yl)-2,2-diMethylpropanoate
• CAS No.: 189239-02-9
• Molecular Formula: C36H39ClN2O3S
• Molecular Weight: 615.22
• Mol file: 189239-02-9.mol

Synonyms:3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester;1H-Indole-2-propanoic acid, 1-[(4-chlorophenyl)methyl]-3-[(1,1-dimethylethyl)thio]-Alpha,Alpha-dimethyl-5-(2-quinolinylmethoxy)-, ethyl ester;1H-Indole-2-propanoic acid, 1-[(4-chlorophenyl)methyl]-3-[(1,1-dimethylethyl)thio]-α,α-dimethyl-5-(2-quinolinylmethoxy)-, ethyl ester;

Chemical Property of ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylMethoxy)-1H-indol-2-yl)-2,2-diMethylpropanoate

Chemical Property:

• PSA: 78.65000
• LogP: 9.49260

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylMethoxy)-1H-indol-2-yl)-2,2-diMethylpropanoate

There total 5 articles about ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylMethoxy)-1H-indol-2-yl)-2,2-diMethylpropanoate 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: 84.0%

2-(chloromethyl)quinoline monohydrochloride (3747-74-8) + ethyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropionate (154325-77-6) → 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester (189239-02-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; a) 60 deg C, 3 h, b) RT, 15 h;

DOI:10.1016/S0968-0896(96)00265-9

Reference yield:

4-methoxyphenylhydrazine hydrochloride (19501-58-7) → 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester (189239-02-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / diisopropylamine, tetrabutylammonium bromide / CH₂Cl₂ / 48 h / Ambient temperature

2: 50 percent / acetic acid / toluene / 96 h / Ambient temperature

3: 70 percent / AlCl₃, t-BuSH / CH₂Cl₂ / a) 0 deg C, 10 min, b) RT, 3 h

4: 84 percent / K₂CO₃ / dimethylformamide / a) 60 deg C, 3 h, b) RT, 15 h

With aluminium trichloride; tetrabutylammomium bromide; potassium carbonate; 2-methylpropan-2-thiol; acetic acid; diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(96)00265-9

Reference yield:

1-(4-chlorobenzyl)-1-(4-methoxyphenyl)hydrazine (62646-04-2) → 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid ethyl ester (189239-02-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / acetic acid / toluene / 96 h / Ambient temperature

2: 70 percent / AlCl₃, t-BuSH / CH₂Cl₂ / a) 0 deg C, 10 min, b) RT, 3 h

3: 84 percent / K₂CO₃ / dimethylformamide / a) 60 deg C, 3 h, b) RT, 15 h

With aluminium trichloride; potassium carbonate; 2-methylpropan-2-thiol; acetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(96)00265-9

upstream raw materials:

2-(chloromethyl)quinoline monohydrochloride

ethyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropionate

4-methoxyphenylhydrazine hydrochloride

1-(4-chlorobenzyl)-1-(4-methoxyphenyl)hydrazine

Downstream raw materials:

O-{3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propyl}-hydroxylamine

3-[3-(1,1-dimethylethylthio)-5-(quinolin-2-ylmethoxy)-1-(4-chlorophenylmethyl)indol-2-yl]-2,2-dimethylpropanol

Refernces