4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one

Base Information

• Chemical Name: 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one
• CAS No.: 1357192-60-9
• Molecular Formula: C₂₆H₂₂FN₅O₃
• Molecular Weight: 471.491
• Mol file: 1357192-60-9.mol

Synonyms:4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one

Chemical Property of 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one

There total 13 articles about 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-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: 35.0%

4'-fluoro-5'-{2-[3-methoxy-2-oxo-1-(1-phenyl-1H-pyrazol-5-yl)propylidene]hydrazino}-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one (1357192-60-9)

Guidance literature:

In acetonitrile; Reflux;

DOI:10.1016/j.bmc.2015.10.002

Reference yield:

diethyl (2-fluoro-6-nitrophenyl)malonate → 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one (1357192-60-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: hydrogenchloride / water; acetic acid / 6 h / Reflux

2.1: thionyl chloride / 3 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 0 °C

4.1: zinc / acetic acid / 4 h / 100 °C

5.1: nitric acid; sulfuric acid / 4 h / -40 - 20 °C

6.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C

7.1: hydrogen; 5%-palladium/activated carbon / methanol / 20 °C

8.1: hydrogenchloride; sodium nitrite / water / 0.25 h / 0 °C

8.2: 0 °C

9.1: acetonitrile / Reflux

With hydrogenchloride; thionyl chloride; sulfuric acid; 5%-palladium/activated carbon; hydrogen; nitric acid; sodium hydride; zinc; sodium nitrite; In tetrahydrofuran; methanol; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2015.10.002

Reference yield:

(2-fluoro-6-nitrophenyl)acetic acid (136916-19-3) → 4′-fluoro-5′-[5-methoxy-4-oxo-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-1(4H)-yl]-1'-methylspiro[cyclobutane-1,3'-indol]-2'(1'H)-one (1357192-60-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: thionyl chloride / 3 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 0 °C

3.1: zinc / acetic acid / 4 h / 100 °C

4.1: nitric acid; sulfuric acid / 4 h / -40 - 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C

6.1: hydrogen; 5%-palladium/activated carbon / methanol / 20 °C

7.1: hydrogenchloride; sodium nitrite / water / 0.25 h / 0 °C

7.2: 0 °C

8.1: acetonitrile / Reflux

With hydrogenchloride; thionyl chloride; sulfuric acid; 5%-palladium/activated carbon; hydrogen; nitric acid; sodium hydride; zinc; sodium nitrite; In tetrahydrofuran; methanol; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2015.10.002

upstream raw materials:

1,2-difluoro-3-nitrobenzene

(2-fluoro-6-nitrophenyl)acetic acid

methyl (2-fluoro-6-nitrophenyl)acetate

methyl 1-(2-fluoro-6-nitrophenyl)cyclobutanecarboxylate