2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene

Base Information

• Chemical Name: 2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene
• CAS No.: 921596-18-1
• Molecular Formula: C₁₆H₁₀F₇NS
• Molecular Weight: 381.317
• Mol file: 921596-18-1.mol

Synonyms:2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene

Chemical Property of 2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene

There total 1 articles about 2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene 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:

4-bromo-2-methylthiophene (29421-92-9) → 2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene (921596-18-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / Ni(dppp)Cl₂ / diethyl ether / 22 h

2.1: AcONa

3.1: triisopropyl borate

4.1: 87 percent / PPh₃; aq. Na₂CO₃ / Pd(dba)2 / tetrahydrofuran / Heating

5.1: BuLi / tetrahydrofuran / 0.33 h / -78 °C

5.2: 83 percent / tetrahydrofuran / 0.5 h / -78 °C

With n-butyllithium; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); Triisopropyl borate; sodium acetate; sodium carbonate; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether;

DOI:10.1002/anie.200602591

Reference yield:

2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene (921596-18-1) + N-tert-butoxycarbonyl-4-[4-(3,5-dimethyl-4-bromothiophen-2-yl)phenoxymethyl]piperidine (921596-17-0) → 4-(4-{4-[2-(2,4-dimethyl-5-pyridin-4-yl-thiophen-3-yl)-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl]-3,5-dimethyl-thiophen-2-yl}-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (921596-08-9) + 4-[4-(4,4,5,5,6,6-hexafluoro-3,7,9a,9b-tetramethyl-8-pyridin-4-yl-5,6,9a,9b-tetrahydro-4H-1,9-dithia-trinden-2-yl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:

N-tert-butoxycarbonyl-4-[4-(3,5-dimethyl-4-bromothiophen-2-yl)phenoxymethyl]piperidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Title compound not separated from byproducts;

DOI:10.1002/anie.200602591

Reference yield:

2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene (921596-18-1) + N-tert-butoxycarbonyl-4-[4-[5-(3,5-dimethyl-4-bromothiophen-2-yl)thiophen-2-yl]phenoxy]piperidine (921596-21-6) → 4-[4-(2-{3,5-dimethyl-5'-[4-(piperidin-4-yloxy)-phenyl]-[2,2']bithiophenyl-4-yl}-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl)-3,5-dimethyl-thiophen-2-yl]-pyridine + 4-(4,4,5,5,6,6-hexafluoro-3,7,9a,9b-tetramethyl-8-{5-[4-(piperidin-4-yloxy)-phenyl]-thiophen-2-yl}-5,6,9a,9b-tetrahydro-4H-1,9-dithia-trinden-2-yl)-pyridine

Guidance literature:

N-tert-butoxycarbonyl-4-[4-[5-(3,5-dimethyl-4-bromothiophen-2-yl)thiophen-2-yl]phenoxy]piperidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

2,4-dimethyl-3-(perfluorocyclopenten-1-yl)-5-(4-pyridyl)thiophene; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With hydrogenchloride; In dichloromethane; at 20 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1002/anie.200602591

upstream raw materials:

4-bromo-2-methylthiophene

Downstream raw materials:

4-(4-{4-[2-(2,4-dimethyl-5-pyridin-4-yl-thiophen-3-yl)-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl]-3,5-dimethyl-thiophen-2-yl}-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

4-(4-{4'-[2-(2,4-dimethyl-5-pyridin-4-yl-thiophen-3-yl)-3,3,4,4,5,5-hexafluoro-cyclopent-1-enyl]-3',5'-dimethyl-[2,2']bithiophenyl-5-yl}-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester