toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester
• CAS No.: 1357263-63-8
• Molecular Formula: C₄₀H₃₉N₅O₅S
• Molecular Weight: 701.846
• Mol file: 1357263-63-8.mol

Synonyms:toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester

Chemical Property of toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester

There total 8 articles about toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl 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: 92.0%

5-[6'-(3-{3-[3-(6-azidohexyloxy)phenyl]prop-2-ynyloxy}prop-1-ynyl)[2,2']bipyridinyl-6-yl]-pent-4-yn-1-ol (1357263-62-7) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester (1357263-63-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1002/anie.201105012

Reference yield:

3-Iodophenol (626-02-8) → toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester (1357263-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 0.33 h / 65 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation

2: copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / methanol / 0.33 h / 65 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation

3: caesium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

4: triethylamine / dichloromethane / 18 h / 0 - 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Sonogashira coupling / 2: Sonogashira coupling;

DOI:10.1002/anie.201105012

Reference yield:

6,6'-Dibromo-2,2'-bipyridine (49669-22-9) → toluene-4-sulfonic acid 5-[6'-(3-(3-[3-(6-azido-hexyloxy)-phenyl]-prop-2-ynyloxy)-prop-1-ynyl)-[2,2']bipyridinyl-6-yl]-pent-4-ynyl ester (1357263-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / methanol; toluene / 18 h / Inert atmosphere; Reflux

2: copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / methanol / 0.33 h / 65 °C / 760.05 Torr / Inert atmosphere; Microwave irradiation

3: caesium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

4: triethylamine / dichloromethane / 18 h / 0 - 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; caesium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Sonogashira coupling / 2: Sonogashira coupling;

DOI:10.1002/anie.201105012

upstream raw materials:

3-(3-(3-[6'-(5-hydroxy-pent-1-ynyl)-[2,2']bipyridinyl-6-yl]-prop-2-ynyloxy)prop-1-ynyl)phenol

5-[6'-(3-{3-[3-(6-azidohexyloxy)phenyl]prop-2-ynyloxy}prop-1-ynyl)[2,2']bipyridinyl-6-yl]-pent-4-yn-1-ol

p-toluenesulfonyl chloride

5-(6'-bromo-[2,2']bipyridinyl-6-yl)-pent-4-yn-1-ol

Downstream raw materials:

C₈₉H₈₄N₈O₆