thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester

Base Information

• Chemical Name: thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester
• CAS No.: 475666-93-4
• Molecular Formula: C₃₀H₁₈N₄O₆S₂
• Molecular Weight: 594.628

Synonyms:thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester

Chemical Property of thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester

Chemical Property:

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Technology Process of thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester

There total 4 articles about thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} 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: 69.0%

1-iodo-4-thioacetylbenzene (69746-43-6) + 3,3'-dinitro-5,5'-bis-phenylethynyl-[2,2']bipyridinyl (857256-62-3) → thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester (475666-93-4)

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/j.tet.2003.09.004

Reference yield:

2-Chloro-3-nitropyridine (5470-18-8,34515-82-7) → thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester (475666-93-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper bronze / dimethylformamide / 5.5 h / 145 °C

2.1: hydrogen bromide / methanol; CH₂Cl₂

2.2: 3.46 g / bromine / 24 h / Heating

3.1: 48 percent / copper(I) iodide; bis(triphenylphosphine)palladium(II) dichloride; diisopropylethylamine / tetrahydrofuran / 16 h

4.1: 69 percent / copper(I) iodide; triphenylphosphine; diisopropylethylamine / bis(dibenzylideneacetone)palladium / tetrahydrofuran / 1 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; hydrogen bromide; copper; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Ullmann coupling / 3.1: Castro-Stephens/Sonogashira coupling / 4.1: Castro-Stephens/Sonogashira coupling;

DOI:10.1016/j.tet.2003.09.004

Reference yield:

3,3’-dinitro-2,2’-bipyridine (1024-94-8) → thioacetic acid S-{4-[5'-(4-acetylsulfanyl-phenylethynyl)-3,3'-dinitro-[2,2']bipyridinyl-5-ylethynyl]-phenyl} ester (475666-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen bromide / methanol; CH₂Cl₂

1.2: 3.46 g / bromine / 24 h / Heating

2.1: 48 percent / copper(I) iodide; bis(triphenylphosphine)palladium(II) dichloride; diisopropylethylamine / tetrahydrofuran / 16 h

3.1: 69 percent / copper(I) iodide; triphenylphosphine; diisopropylethylamine / bis(dibenzylideneacetone)palladium / tetrahydrofuran / 1 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; hydrogen bromide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; 2.1: Castro-Stephens/Sonogashira coupling / 3.1: Castro-Stephens/Sonogashira coupling;

DOI:10.1016/j.tet.2003.09.004

upstream raw materials:

1-iodo-4-thioacetylbenzene

3,3'-dinitro-5,5'-bis-phenylethynyl-[2,2']bipyridinyl

2-Chloro-3-nitropyridine

3,3’-dinitro-2,2’-bipyridine

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