3-cyano-1H-Indole-6-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-cyano-1H-Indole-6-carboxylic acid methyl ester
• CAS No.: 1000576-51-1
• Molecular Formula: C₁₁H₈N₂O₂
• Molecular Weight: 200.197
• Hs Code.: 2933990090
• Mol file: 1000576-51-1.mol

Synonyms:Methyl 3-cyanoindole-6-carboxylate;

Chemical Property of 3-cyano-1H-Indole-6-carboxylic acid methyl ester

Chemical Property:

• Boiling Point: 413.5±25.0 °C(Predicted)
• PKA: 13.41±0.30(Predicted)
• PSA: 65.88000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 1.82618
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Methyl3-cyanoindole-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-cyano-1H-Indole-6-carboxylic acid methyl ester

There total 2 articles about 3-cyano-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: 82.0%

indole-6-carboxylic acid methyl ester (50820-65-0) + phenylacetonitrile (140-29-4) → methyl 3-cyano-1H-indole-6-carboxylate (1000576-51-1)

Guidance literature:

With copper(l) iodide; In N,N-dimethyl-formamide; at 100 ℃; for 34h;

DOI:10.1016/j.tet.2013.03.089

Reference yield:

isocyanate de chlorosulfonyle (1189-71-5) + indole-6-carboxylic acid methyl ester (50820-65-0) → methyl 3-cyano-1H-indole-6-carboxylate (1000576-51-1)

Guidance literature:

In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2013.04.050

Reference yield:

methyl 3-cyano-1H-indole-6-carboxylate (1000576-51-1) → C20H19N3O4S (944563-59-1)

Guidance literature:

Multi-step reaction with 5 steps

1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

2: lithium diisopropyl amide; Triisopropyl borate / tetrahydrofuran / -78 - 20 °C

3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 20 °C

4: pyridine / dichloromethane / 20 °C

5: sodium hydroxide / methanol / 1 h / 60 °C

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Triisopropyl borate; potassium carbonate; caesium carbonate; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.04.050

upstream raw materials:

indole-6-carboxylic acid methyl ester

phenylacetonitrile

isocyanate de chlorosulfonyle

Downstream raw materials:

C₁₉H₁₇N₃O₂

C₂₁H₂₁N₃O₄S

C₂₀H₁₉N₃O₄S

C₂₀H₂₀N₄O₃S

Refernces

• 1、 Chen, Guangming,Ren, Hongyu,Turpoff, Anthony,Arefolov, Alexander,Wilde, Richard,Takasugi, James,Khan, Atiyya,Almstead, Neil,Gu, Zhengxian,Komatsu, Takashi,Freund, Connie,Breslin, Jamie,Colacino, Joseph,Hedrick, Jean,Weetall, Marla,Karp, Gary M.. "Discovery of N-(4′-(indol-2-yl)phenyl)sulfonamides as novel inhibitors of HCV replication". . p. 3942 - 3946. Retrieved 2013/07/27.