(S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

Base Information

Chemical Name:(S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide
CAS No.:1581755-89-6
Molecular Formula:C₂₅H₂₃N₃O₃
Molecular Weight:413.476
Hs Code.:

Synonyms:(S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

Chemical Property:

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Technology Process of (S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

There total 5 articles about (S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide 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: 68.0%

: 35447-83-7
N-(4-ethynylphenyl)acetamide

: 1581755-85-2
(S)-6-(hydroxymethyl)-4-iodo-N-(1-phenylethyl)picolinamide

: 1581755-89-6
(S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 65 ℃; for 24h; Inert atmosphere;
DOI:10.1039/c3dt53000k

Reference yield:

: 75867-39-9
4-trimethylsilylethynyl aniline

: 1581755-89-6
(S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

Guidance literature:: Multi-step reaction with 3 steps

1: dichloromethane / 20 °C / Inert atmosphere

2: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 48 h / 35 °C / Inert atmosphere

3: triethylamine; copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 24 h / 65 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; dichloromethane; 3: |Sonogashira Cross-Coupling;
DOI:10.1039/c3dt53000k

Reference yield:

: 1247012-08-3
methyl 6-(hydroxymethyl)-4-iodopicolinate

: 1581755-89-6
(S)-4-((4-acetamidophenyl)ethynyl)-6-(hydroxymethyl)-N-(1-phenylethyl)picolinamide

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydroxide / water; ethanol / 20 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; dichloromethane / 22 h / 20 °C / Inert atmosphere

3: triethylamine; copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 24 h / 65 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;
DOI:10.1039/c3dt53000k