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

Base Information

• Chemical Name: 4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1357588-08-9
• Molecular Formula: C₃₄H₃₅F₃N₆O₅S
• Molecular Weight: 696.75
• Mol file: 1357588-08-9.mol

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

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

There total 9 articles about 4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-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: 35.0%

4-iodo-1H-pyrrolo[2,3-b]pyridine (319474-34-5) + 4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester (1357588-07-8) → 4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester (1357588-08-9)

Guidance literature:

With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,2-dimethoxyethane; water; at 90 ℃; for 1h; Inert atmosphere; Microwave irradiation;

Reference yield:

3-bromo-2-fluorobenzenamine (58534-95-5) → 4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester (1357588-08-9)

Guidance literature:

Multi-step reaction with 8 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: triethylamine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / bis(acetonitrile)palladium(II) dichloride / toluene / 0.5 h / 90 °C / Inert atmosphere; Microwave irradiation

8: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane; water / 1 h / 90 °C / Inert atmosphere; Microwave irradiation

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; pyridine; N-Bromosuccinimide; caesium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis(acetonitrile)palladium(II) dichloride; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

2,5-difluorobenzenesulfonyl chloride (26120-86-5) → 4-[3-{3-[(2,5-difluorobenzenesulfonyl)methoxymethylamino]-2-fluorophenyl}-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester (1357588-08-9)

Guidance literature:

Multi-step reaction with 8 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: triethylamine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / bis(acetonitrile)palladium(II) dichloride / toluene / 0.5 h / 90 °C / Inert atmosphere; Microwave irradiation

8: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,2-dimethoxyethane; water / 1 h / 90 °C / Inert atmosphere; Microwave irradiation

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; pyridine; N-Bromosuccinimide; caesium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis(acetonitrile)palladium(II) dichloride; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2,5-difluorobenzenesulfonyl chloride

4-iodo-1H-pyrrolo[2,3-b]pyridine

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

3-bromo-2-fluorobenzenamine

Downstream raw materials:

2,5-difluoro-N-{2-fluoro-3-[1-(1-methylpiperidin-4-yl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}benzenesulfonamide