3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile

Base Information

• Chemical Name: 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile
• CAS No.: 1094342-52-5
• Molecular Formula: C₂₀H₁₁Cl₂FN₄O₃S
• Molecular Weight: 477.303
• Mol file: 1094342-52-5.mol

Synonyms:3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile

Chemical Property of 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile

There total 12 articles about 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile 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: 47.0%

3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-2-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile (1094342-50-3) → 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile (1094342-52-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 60 ℃; for 21h; Reflux;

Reference yield:

ethyl 2-chloro-4-methylthiazole-5-carboxylate (7238-62-2) → 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile (1094342-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: caesium carbonate / 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate / toluene / 6 h / 100 °C / Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C

2.2: 2 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 3 h / 20 °C

3.2: 72 h / 20 °C

4.1: pyridinium p-toluenesulfonate / methanol / 21 h / 60 °C / Reflux

With pyridinium p-toluenesulfonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; lithium hydroxide; 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate; In tetrahydrofuran; methanol; toluene;

Reference yield:

3,5-dichlorobenzonitrile (6575-00-4) → 3-chloro-5-[(6-chloro-2-fluoro-3-{[5-(4-methyl-2-oxo-2,3-dihydro-1,3-thiazol-5-yl)-1,3,4-oxadiazol-2-yl]methyl}phenyl)oxy]benzonitrile (1094342-52-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: N,N-dimethyl-formamide / 0 - 20 °C

1.2: 20 °C / Cooling with ice

2.1: 2,4,6-trimethyl-pyridine; lithium iodide / 8 h / 185 °C / Inert atmosphere

2.2: Cooling with ice

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

3.2: 20 °C

3.3: 20 °C / Cooling with ice

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

4.2: 4 h / 0 - 20 °C

4.3: 20 °C

5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 60 °C

5.2: 0 °C

6.1: sodium dithionite; water / tetrahydrofuran / 1 h / 20 °C

7.1: tert.-butylnitrite; copper dichloride / acetonitrile / 0.25 h / 50 °C

8.1: hydrazine / ethanol / 2 h / Reflux

9.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 3 h / 20 °C

9.2: 72 h / 20 °C

10.1: pyridinium p-toluenesulfonate / methanol / 21 h / 60 °C / Reflux

With 2,4,6-trimethyl-pyridine; tert.-butylnitrite; sodium dithionite; water; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; copper dichloride; lithium iodide; hydrazine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

upstream raw materials:

3,5-dichlorobenzonitrile

3-chloro-5-methoxybenzonitrile

3-chloro-5-hydroxybenzonitrile

3-chloro-5-[(2,3-difluoro-6-nitrophenyl)oxy]benzonitrile

Refernces