5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one

Base Information

• Chemical Name: 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one
• CAS No.: 2035814-50-5
• Molecular Formula: C₂₅H₂₂FN₅O₂
• Molecular Weight: 443.48
• Mol file: 2035814-50-5.mol

Synonyms:

Chemical Property of 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one

There total 8 articles about 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one 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:

5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydroindol-2-one (837392-64-0) + C17H16BrFN4O → 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one (2035814-50-5)

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium hydrogencarbonate; In 1,4-dioxane; water; at 110 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.8b00599

Reference yield:

1-(4-fluorophenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone oxime (601521-49-7) → 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one (2035814-50-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic anhydride; triethylamine / 1,2-dimethoxyethane / 1.5 h / 0 - 20 °C / Inert atmosphere

1.2: 8 h / 80 °C / Inert atmosphere

2.1: N-Bromosuccinimide / acetonitrile / 12 h / 0 - 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: N,N-dimethyl acetamide / 16 h / 100 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere

With N-Bromosuccinimide; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl acetamide; water; acetonitrile; 5.1: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.8b00599

Reference yield:

3-bromo-2-(4-fluorophenyl)-7-(methylsulfonyl)pyrazolo[1,5-c]pyrimidine → 5-[2-(4-fluorophenyl)-7-(4-hydroxy-1-piperidyl)pyrazolo[1,5-c]pyrimidin-3-yl]indolin-2-one (2035814-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl acetamide / 16 h / 100 °C / Inert atmosphere

2: sodium hydrogencarbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / 1,4-dioxane; water / 6 h / 110 °C / Inert atmosphere

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium hydrogencarbonate; In 1,4-dioxane; N,N-dimethyl acetamide; water; 2: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.8b00599

upstream raw materials:

5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydroindol-2-one

4-fluorobenzoic acid ethyl ester

1-(4-fluorophenyl)-2-(2-methylsulphanylpyrimidin-4-yl)-1-ethanone

1-(4-fluorophenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone oxime