3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine

Base Information

• Chemical Name: 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine
• CAS No.: 1107616-89-6
• Molecular Formula: C₁₉H₁₇N₃O₂
• Molecular Weight: 319.363
• Mol file: 1107616-89-6.mol

Synonyms:3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine

Chemical Property of 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine

There total 4 articles about 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]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: 57.0%

iodobenzene (591-50-4) + 3-Nitro-2-[4-(prop-2-ynyliden)piperidin-1-yl]pyridine (1107620-19-8) → 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine (1107616-89-6)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; at 80 ℃; for 2h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.bmc.2015.05.008

Reference yield:

1-(3-nitropyridin-2-yl)piperidin-4-one (338411-72-6) → 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine (1107616-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -60 °C / Inert atmosphere

1.2: 2.25 h / -60 - 25 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere

3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / 2 h / 80 °C / Sealed tube; Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination / 3.1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2015.05.008

Reference yield:

3-nitro-2-{4-[3-(trimethylsilyl)prop-2-yn-1-ylidene]piperidin-1-yl}pyridine (1107620-18-7) → 3-nitro-2-[4-(3-phenylprop-2-yn-1-ylidene)piperidin-1-yl]pyridine (1107616-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere

2: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / 2 h / 80 °C / Sealed tube; Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; 2: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2015.05.008

upstream raw materials:

3-nitro-2-{4-[3-(trimethylsilyl)prop-2-yn-1-ylidene]piperidin-1-yl}pyridine

1-(3-nitropyridin-2-yl)piperidin-4-one

iodobenzene

3-Nitro-2-[4-(prop-2-ynyliden)piperidin-1-yl]pyridine

Refernces

• 1、 -. "NOVEL HETEROCYCLIC DERIVATIVES AS M-GLU5 ANTAGONISTS". Page/Page column 31. . Retrieved 2009/03/07.