4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one

Base Information

• Chemical Name: 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one
• CAS No.: 868662-14-0
• Molecular Formula: C₁₈H₁₄ClF₃N₂O₂
• Molecular Weight: 382.77
• Mol file: 868662-14-0.mol

Synonyms:4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one

Chemical Property of 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one

There total 5 articles about 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-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: 82.0%

trifluoro-methanesulfonic acid 5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yl ester (868662-13-9) + 4-trifluoromethylphenylacetylene (705-31-7) → 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one (868662-14-0)

Guidance literature:

trifluoro-methanesulfonic acid 5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yl ester; With copper(l) iodide; tetra-(n-butyl)ammonium iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 0.00277778h;

4-trifluoromethylphenylacetylene; With triethylamine; In tetrahydrofuran; for 3h;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one (868662-14-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / TsOH / tetrahydrofuran / Heating

2: 83 percent / KOH

3: 75 percent / aq. KOH / Heating

4: TEA / CH₂Cl₂ / 0.5 h / 0 °C

5: 467 mg / Pd(PPh₃)2Cl₂; CuI; tetra-n-butylammonium iodide / TEA / tetrahydrofuran / 3 h

With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; copper(l) iodide; TEA; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; TEA; In tetrahydrofuran; dichloromethane; 5: Sonogashira coupling;

DOI:10.1021/jm051263c

Reference yield:

4-chloro-5-methoxy-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone (173206-12-7) → 4-chloro-2-(tetrahydropyran-2-yl)-5-(4-trifluoromethylphenylethynyl)-2H-pyridazin-3-one (868662-14-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / aq. KOH / Heating

2: TEA / CH₂Cl₂ / 0.5 h / 0 °C

3: 467 mg / Pd(PPh₃)2Cl₂; CuI; tetra-n-butylammonium iodide / TEA / tetrahydrofuran / 3 h

With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; copper(l) iodide; TEA; tetra-(n-butyl)ammonium iodide; TEA; In tetrahydrofuran; dichloromethane; 3: Sonogashira coupling;

DOI:10.1021/jm051263c

upstream raw materials:

trifluoro-methanesulfonic acid 5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yl ester

4-trifluoromethylphenylacetylene

3,4-dihydro-2H-pyran

4,5-dichloro-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone

Downstream raw materials:

6-(tetrahydro-pyran-2-yl)-2-(4-trifluoromethyl-phenyl)-6H-furo[2,3-d]pyridazin-7-one

6-(tetrahydro-pyran-2-yl)-2-(4-trifluoromethyl-phenyl)-6H-thieno[2,3-d]pyridazin-7-one

6-(tetrahydro-pyran-2-yl)-2-(4-trifluoromethyl-phenyl)-6H-selenolo[2,3-d]pyridazin-7-one

4-methylamino-2-(tetrahydro-pyran-2-yl)-5-(4-trifluoromethyl-phenylethynyl)-2H-pyridazin-3-one