4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1357587-67-7
• Molecular Formula: C₃₂H₃₄F₃N₅O₅S
• Molecular Weight: 657.714

Synonyms:4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

There total 8 articles about 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester 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: 43.0%

4-(4-bromo-3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1357587-65-5) + 4-pyridineboronic acid pinacol ester (181219-01-2) → 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1357587-67-7)

Guidance literature:

With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; water; at 100 ℃; for 2h; Inert atmosphere;

Reference yield:

3-bromo-2-fluorobenzenamine (58534-95-5) → 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1357587-67-7)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.17 h / 0 - 20 °C

3: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere

4: toluene-4-sulfonic acid / methanol / 1 h / 20 °C

5: N-Bromosuccinimide / dichloromethane / 1.5 h / 20 °C

6: caesium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C

7: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

2,5-difluorobenzenesulfonyl chloride (26120-86-5) → 4-(3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-pyridin-4-ylpyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (1357587-67-7)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.17 h / 0 - 20 °C

3: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere

4: toluene-4-sulfonic acid / methanol / 1 h / 20 °C

5: N-Bromosuccinimide / dichloromethane / 1.5 h / 20 °C

6: caesium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C

7: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

2,5-difluorobenzenesulfonyl chloride

4-(4-bromo-3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

4-pyridineboronic acid pinacol ester

3-bromo-2-fluorobenzenamine

Downstream raw materials:

N-{3-[1-(1-acetylpiperidin-4-yl)-4-pyridin-4-yl-1H-pyrazol-3-yl]-2-fluorophenyl}-2,5-difluoro-N-methoxymethylbenzenesulfonamide

N-{3-[4-(2-aminopyridin-4-yl)-1-(1-methylpiperidin-4-yl)-1H-pyrazol-3-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

N-{3-[4-(2-tert-butylaminopyridin-4-yl)-1-(1-methylpiperidin-4-yl)-1H-pyrazol-3-yl]-2-fluorophenyl}-2,5-difluoro-N-methoxymethylbenzenesulfonamide

4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(1-oxypyridin-4-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester

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