methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

Base Information

Chemical Name:methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate
CAS No.:1581755-87-4
Molecular Formula:C₂₅H₂₂N₂O₄
Molecular Weight:414.461
Hs Code.:

Synonyms:methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

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Chemical Property of methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

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Technology Process of methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

There total 3 articles about methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate 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: 89.0%

: 3034-86-4
4-ethynylbenzoic acid methyl ester

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

: 1581755-87-4
methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

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:

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

: 1581755-87-4
methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

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

Reference yield:

: 1581755-84-1
6-(hydroxymethyl)-4-iodopicolinic acid

: 1581755-87-4
methyl (S)-4-((2-(hydroxymethyl)-6-(1-phenylethylcarbamoyl)-pyridin-4-yl)ethynyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 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

2: 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; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;
DOI:10.1039/c3dt53000k