3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

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Chemical Name:3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile
CAS No.:1403612-36-1
Molecular Formula:C₁₄H₅F₂IN₄O
Molecular Weight:410.121
Hs Code.:

Synonyms:3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

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Chemical Property of 3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

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Technology Process of 3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

There total 10 articles about 3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile 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: 96.0%

: 1403612-35-0
N'-[(3-cyano-5-fluoro-4-iodobenzoyl)oxy]-5-fluoropyridine-2-carboximidamide

: 1403612-36-1
3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

Guidance literature:: With pyridine; at 120 ℃; for 4h;
DOI:10.1016/j.bmcl.2012.08.100

Reference yield:

: 1435-51-4
1,3-dibromo-5-fluorobenzene

: 1403612-36-1
3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine / N,N-dimethyl-formamide / 4.5 h / 150 °C / Inert atmosphere

2.1: water; sodium hydroxide / 2 h / Reflux

3.1: thionyl chloride / 2 h / 70 °C

4.1: triethylamine / 2.08 h / 0 - 20 °C

5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; zinc / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux

6.1: 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium; zinc(II) chloride / tetrahydrofuran; diethyl ether; hexane; pentane / 3 h / 0 °C / Inert atmosphere

6.2: 3 h / 20 °C

7.1: water; lithium hydroxide / acetonitrile / 1 h

8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2.25 h

9.1: pyridine / 4 h / 120 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; water; tert.-butyl lithium; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc(II) chloride; lithium hydroxide; zinc; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetonitrile; pentane;
DOI:10.1016/j.bmcl.2012.08.100

Reference yield:

: 179898-34-1
3-bromo-5-fluorobenzonitrile

: 1403612-36-1
3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]-2-iodobenzonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: water; sodium hydroxide / 2 h / Reflux

2.1: thionyl chloride / 2 h / 70 °C

3.1: triethylamine / 2.08 h / 0 - 20 °C

4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; zinc / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux

5.1: 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium; zinc(II) chloride / tetrahydrofuran; diethyl ether; hexane; pentane / 3 h / 0 °C / Inert atmosphere

5.2: 3 h / 20 °C

6.1: water; lithium hydroxide / acetonitrile / 1 h

7.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2.25 h

8.1: pyridine / 4 h / 120 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; water; tert.-butyl lithium; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc(II) chloride; lithium hydroxide; zinc; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetonitrile; pentane;
DOI:10.1016/j.bmcl.2012.08.100