Methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate

Base Information

• Chemical Name: Methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate
• CAS No.: 473257-71-5
• Molecular Formula: C18H16ClNO2S
• Molecular Weight: 345.85
• DSSTox Substance ID: DTXSID801159840
• Mol file: 473257-71-5.mol

Synonyms:SCHEMBL4405329;MYQAIDPJYKRWOH-UHFFFAOYSA-N;DTXSID801159840;methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate;473257-71-5;Methyl 5-chloro-3-[(3,5-dimethylphenyl)thio]-1H-indole-2-carboxylate

Chemical Property of Methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate

Chemical Property:

• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 345.0590276
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)SC2=C(NC3=C2C=C(C=C3)Cl)C(=O)OC)C

Technology Process of Methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-carboxylate

There total 2 articles about Methyl 5-chloro-3-(3,5-dimethylphenylthio)indole-2-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: 77.0%

methyl 5-chloroindole-2-carboxylate (87802-11-7) + 1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione (473258-21-8) → methyl 5-chloro-3-[(3,5-dimethylphenyl)thio]-1H-indole-2-carboxylate (473257-71-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 - 45 ℃; for 4h;

DOI:10.1021/jm0211063

Reference yield:

3,5-Dimethylthiophenol (38360-81-5) → methyl 5-chloro-3-[(3,5-dimethylphenyl)thio]-1H-indole-2-carboxylate (473257-71-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / CH₂Cl₂ / 3.5 h

2: 77 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 20 - 45 °C

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/jm0211063

Reference yield: 91.0%

methyl 5-chloro-3-[(3,5-dimethylphenyl)thio]-1H-indole-2-carboxylate (473257-71-5) → 5-chloro-3-(3,5-dimethyl-phenylsulfanyl)-1H-indole-2-carboxylic acid amide

Guidance literature:

With ammonium hydroxide; ammonium chloride; at 100 ℃;

DOI:10.1021/jm0211063

upstream raw materials:

methyl 5-chloroindole-2-carboxylate

1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione

3,5-Dimethylthiophenol

Downstream raw materials:

methyl 5-chloro-3-[(3,5-dimethylphenyl)sulfonyl]-1H-indole-2-carboxylate

5-chloro-3-(3,5-dimethyl-benzenesulfonyl)-1H-indole-2-carboxylic acid hydrazide

5-chloro-3-(3,5-dimethylphenyl-sulfonyl)indole-2-carboxylic acid