2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile

Base Information

• Chemical Name: 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile
• CAS No.: 749928-78-7
• Molecular Formula: C₂₅H₂₈FNO₄
• Molecular Weight: 425.5
• Mol file: 749928-78-7.mol

Synonyms:2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile

Chemical Property of 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile

There total 7 articles about 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile 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: 79.0%

6-(2-cyclopentyl-2-hydroxybut-3-ynyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (612062-72-3,749929-95-1,749929-97-3) + 2-(4-bromo-2-fluoro-phenyl)-2-methyl-propionitrile (749928-77-6) → 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile (749928-78-7)

Guidance literature:

With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 20 - 90 ℃; for 0.5h;

Reference yield: 74.0%

→ 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile (749928-78-7)

Guidance literature:

Reference yield:

6-(2-cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl[1,3]dioxin-4-one (612062-71-2) → 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile (749928-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.6 g / CsF / methanol / 25 °C

2: diisopropylamine / bis(triphenylphosphine)palladium (II) dichloride; CuI / dimethylformamide / 0.33 h / 90 °C / sonification

With diisopropylamine; cesium fluoride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In methanol; N,N-dimethyl-formamide; 2: Sonogashira coupling;

DOI:10.1021/jm0704447

upstream raw materials:

6-(2-cyclopentyl-2-hydroxybut-3-ynyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

2-(4-bromo-2-fluoro-phenyl)-2-methyl-propionitrile

6-(2-cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl[1,3]dioxin-4-one

2,2,6-trimethyl-4H-1,3-dioxin-4-one

Downstream raw materials:

2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybutyl]-2-fluorophenyl}-2-methyl-propionitrile

2-{4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-2-methyl-propionitrile

2-[4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-methylpropanenitrile

2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile