6-CYANO-1H-INDOLE, N-BOC PROTECTED 98

Base Information

• Chemical Name: 6-CYANO-1H-INDOLE, N-BOC PROTECTED 98
• CAS No.: 889676-34-0
• Molecular Formula: C14H14N2O2
• Molecular Weight: 242.2766
• Hs Code.: 2933990090
• Mol file: 889676-34-0.mol

Synonyms:1-Boc-6-cyanoindole;N-tert-Butoxycarbonyl-6-cyanoindole;

Chemical Property of 6-CYANO-1H-INDOLE, N-BOC PROTECTED 98

Chemical Property:

• Vapor Pressure: 3.56E-06mmHg at 25°C
• Melting Point: 124-126°C
• Refractive Index: 1.564
• Boiling Point: 386.4 °C at 760 mmHg
• Flash Point: 187.5 °C
• PSA: 55.02000
• Density: 1.12g/cm³
• LogP: 3.29618
• Storage Temp.: Keep Cold

Purity/Quality:

98% purity ^*data from raw suppliers

1-BOC-6-cyanoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-CYANO-1H-INDOLE, N-BOC PROTECTED 98

There total 6 articles about 6-CYANO-1H-INDOLE, N-BOC PROTECTED 98 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: 87.0%

1H-Indole-6-carbonitrile (15861-36-6) + di-tert-butyl dicarbonate (24424-99-5) → 1-(tert-butoxycarbonyl)-1H-indole-6-carbonitrile (889676-34-0)

Guidance literature:

With dmap; In dichloromethane; at 0 - 5 ℃; for 2h;

DOI:10.1055/s-2008-1032162

Reference yield: 80.0%

potassium cyanide + C17H22F3NO5SSi (1259448-49-1) → 1-(tert-butoxycarbonyl)-1H-indole-6-carbonitrile (889676-34-0)

Guidance literature:

With cesium fluoride; In acetonitrile; at 50 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ja1086485

Reference yield:

1-(tert-butoxycarbonyl)-6-cyano-1H-indol-2-ylboronic acid (913835-67-3) + 1-(Bromomethyl)-3-fluorobenzene (456-41-7) → 1-(tert-butoxycarbonyl)-1H-indole-6-carbonitrile (889676-34-0) + 6-cyano-2-(3-fluoro-benzyl)-indole-1-carboxylic acid tert-butyl ester (1227625-69-5)

Guidance literature:

With trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); sodium carbonate; In tetrahydrofuran; at 60 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.02.124

upstream raw materials:

1H-Indole-6-carbonitrile

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)-6-cyano-1H-indol-2-ylboronic acid

1-(Bromomethyl)-3-fluorobenzene

Downstream raw materials:

1-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-1H-indole-6-carbonitrile

1-(tert-butoxycarbonyl)-2-(4'-cyanobiphenyl-4-yl)-1hindole-6-carbonitrile

1-(tert-butoxycarbonyl)-2-(biphenyl-4-yl)-1H-indole-6-carbonitrile

Refernces

• 1、 Farahat, Abdelbasset A.,Kumar, Arvind,Say, Martial,Wenzler, Tanja,Brun, Reto,Paul, Ananya,Wilson, W. David,Boykin, David W.. "Exploration of DAPI analogues: Synthesis, antitrypanosomal activity, DNA binding and fluorescence properties". . p. 70 - 78. Retrieved 2017/02/18.
• 2、 Kearney, Aaron M.,Landry-Bayle, Adrienne,Gomez, Laurent. "Palladium-catalyzed benzylation of N-Boc indole boronic acids". scheme or table. p. 2281 - 2283. Retrieved 2010/05/18.