2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine

Base Information

• Chemical Name: 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine
• CAS No.: 349659-52-5
• Molecular Formula: C₁₈H₁₆ClNSi
• Molecular Weight: 309.87
• Mol file: 349659-52-5.mol

Synonyms:2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine

Chemical Property of 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine

There total 4 articles about 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine 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: 80.0%

1-iodo-2-ethynylbenzene (137648-47-6) + 2-chloro-5-ethynylpyridine (263012-63-1) → 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine (349659-52-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20 ℃; for 48h;

DOI:10.1021/jo001777d

Reference yield:

2-choro-5-iodopyridine (69045-79-0) → 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine (349659-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / 48 h / 20 °C

2: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 24 h / 20 °C

3: 80 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 48 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; triethylamine; In tetrahydrofuran; methanol; 1: Sonogashira reaction;

DOI:10.1021/jo001777d

Reference yield:

2-bromo-1-(trimethylsilylethynyl)benzene (38274-16-7) → 2-chloro-5-[(2-trimethylsilylethynylphenyl)ethynyl]pyridine (349659-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / diethyl ether / 3 h / -78 - 0 °C

1.2: 95 percent / 1,2-diiodoethane / diethyl ether / -78 - 0 °C

2.1: 80 percent / PdCl₂(PPh₃)2; CuI; Et₃N / 48 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; triethylamine; In diethyl ether;

DOI:10.1021/jo001777d

upstream raw materials:

1-iodo-2-ethynylbenzene

2-chloro-5-ethynylpyridine

2-choro-5-iodopyridine

2-bromo-1-(trimethylsilylethynyl)benzene

Downstream raw materials:

2-chloro-5-[(2-ethynylphenyl)ethynyl]pyridine

5,5'-bis[(2-trimethylsilylethynylphenyl)ethynyl]-2,2'-bipyridine

5,5'-bis[(2-ethynylphenyl)ethynyl]-2,2'-bipyridine