2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine

Base Information

• Chemical Name: 2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine
• CAS No.: 1311149-70-8
• Molecular Formula: C₂₉H₃₁NO₅SSi
• Molecular Weight: 533.72
• Mol file: 1311149-70-8.mol

Synonyms:2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine

Chemical Property of 2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine

There total 2 articles about 2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine 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: 75.0%

tert-butyl 5-bromofuran-2-carboxylate (59862-83-8) + N-ethynyl-4-methyl-N-(2-((trimethylsilyl)ethynyl)phenyl)benzenesulfonamide (1148038-46-3) → 2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine (1311149-70-8)

Guidance literature:

N-ethynyl-4-methyl-N-(2-((trimethylsilyl)ethynyl)phenyl)benzenesulfonamide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

With zinc dibromide; In tetrahydrofuran; at 22 ℃; for 0.333333h; Inert atmosphere;

tert-butyl 5-bromofuran-2-carboxylate; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In tetrahydrofuran; at 22 ℃; for 23h; Inert atmosphere;

DOI:10.1002/ejoc.201100121

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) → 2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine (1311149-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; dicyclohexyl-carbodiimide

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 0.33 h / 22 °C / Inert atmosphere

2.3: 23 h / 22 °C / Inert atmosphere

With dmap; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1002/ejoc.201100121

Reference yield: 92.0%

2-[2-(trimethylsilyl)ethynyl]-N-{2-[5-(tert-butoxycarbonyl)furan-2-yl]ethynyl}-N-tosylbenzenamine (1311149-70-8) → 2-ethynyl-N-({2-[5-(tert-butoxycarbonyl)furan-2-yl]}ethynyl)-N-tosyl-benzenamine (1311149-34-4) + 2-(tert-butoxycarbonyl)-5-tosylfuro[2,3-b]carbazole (1311149-74-2)

Guidance literature:

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201100121

upstream raw materials:

5-bromo-furan-2-carboxylic acid

tert-butyl 5-bromofuran-2-carboxylate

N-ethynyl-4-methyl-N-(2-((trimethylsilyl)ethynyl)phenyl)benzenesulfonamide

Downstream raw materials:

perlolyrine

methyl 1-[5-(tert-butoxycarbonyl)furan-2-yl]-9-tosyl-9H-pyrido[3,4-b]indole-3-carboxylate

1-[5-(tert-butoxycarbonyl)furan-2-yl]-9-tosyl-9H-pyrido[3,4-b]indole-3-carboxylic acid

1-[5-(tert-butoxycarbonyl)furan-2-yl]-9-tosyl-9H-pyrido[3,4-b]indole-3-carboxylic acid