1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl ester

Base Information

• Chemical Name: 1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl ester
• CAS No.: 132819-92-2
• Molecular Formula: C₁₈H₁₇NO₄S
• Molecular Weight: 343.403
• Mol file: 132819-92-2.mol

Synonyms:1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Chemical Property of 1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl ester

Chemical Property:

• Melting Point: 98-99 °C
• Boiling Point: 523.3±52.0 °C(Predicted)
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

99%+, ^*data from raw suppliers

NOD-IN-1 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl ester

There total 7 articles about 1H-Indole-2-carboxylic acid, 1-[(4-methylphenyl)sulfonyl]-, ethyl 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: 98.0%

2-carbethoxyindole (3770-50-1,117770-52-2) + p-toluenesulfonyl chloride (98-59-9) → 1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (132819-92-2)

Guidance literature:

2-carbethoxyindole; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h; Inert atmosphere;

p-toluenesulfonyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.3762/bjoc.17.101

Reference yield: 63.0%

ethyl (Z)-2-((4-methylphenyl)sulfonamido)-3-phenylacrylate → 1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (132819-92-2)

Guidance literature:

With Oxone; palladium diacetate; In acetic acid; N,N-dimethyl-formamide; at 80 ℃; for 15h; Reagent/catalyst; Solvent; Concentration; Time; Temperature;

DOI:10.5012/bkcs.2014.35.9.2611

Reference yield: 60.0%

ethyl 3-(2-chlorophenyl)-1-tosylaziridine-2-carboxylate → 1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (132819-92-2)

Guidance literature:

ethyl 3-(2-chlorophenyl)-1-tosylaziridine-2-carboxylate; With boron trifluoride diethyl etherate; thiophenol; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

With copper; In dichloromethane; N,N-dimethyl-formamide; at 125 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.joc.5b02251

upstream raw materials:

propionic acid 3-methyl-but-2-enyl ester

ethyl 3-bromo-1-tosylindole-2-carboxylate

propionic acid trans-2-hexen-1-yl ester

2-carbethoxyindole

Downstream raw materials:

1-(p-toluenesulfonyl)-1H-indole-2-carboxyaldehyde

2-carbethoxyindole

Refernces

• 1、 Chelvam, Venkatesh,Dudhe, Premansh,Krishnan, Mena Asha,Pathak, Biswarup,Roy, Diptendu,Venkatasubbaiah, Krishnan,Yadav, Kratika. "Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation". supporting information. p. 1453 - 1463. Retrieved 2021/07/02.
• 2、 Wang, Zheng,Ji, Hongtao,He, Wei-Min,Xiong, Yang,Zhang, Guozhu. "Chromium-Catalyzed Asymmetric Dearomatization-Addition Reactions of Halomethyloxazoles and Indoles". supporting information. p. 4915 - 4921. Retrieved 2018/06/08.