N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

Base Information

Chemical Name:N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide
CAS No.:1135531-76-8
Molecular Formula:C₁₈H₁₅ClF₂N₄O₂
Molecular Weight:392.793
Hs Code.:

Synonyms:N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

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Chemical Property of N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

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Technology Process of N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

There total 12 articles about N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide 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: 66.0%

: 858414-21-8
N-[(1R)-1-(5-bromo-3-fluoropyridin-2-yl)ethyl]acetamide

: 858414-23-0
3-(2-bromo-4-chloro-6-fluorophenyl)-5-methyl-[1,2,4]oxadiazole

: 1135531-76-8
N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

Guidance literature:: N-[(1R)-1-(5-bromo-3-fluoropyridin-2-yl)ethyl]acetamide; With potassium acetate; bis(pinacol)diborane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dimethyl sulfoxide; at 90 ℃; for 1.5h; Inert atmosphere;

3-(2-bromo-4-chloro-6-fluorophenyl)-5-methyl-[1,2,4]oxadiazole; With potassium carbonate; In water; dimethyl sulfoxide; at 20 - 80 ℃; for 3h;

Reference yield:

: 858414-23-0
3-(2-bromo-4-chloro-6-fluorophenyl)-5-methyl-[1,2,4]oxadiazole

: 1135531-75-7
C₁₅H₂₂BFN₂O₃

: 1135531-76-8
N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

Guidance literature:: With potassium phosphate; In water; toluene; at 95 ℃; for 16h; optical yield given as %ee; Large scale reaction;
DOI:10.1021/op8003184

Reference yield:

: 15862-34-7
5-bromo-3-nitro-2-pyridone

: 1135531-76-8
N-[(1R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-3-fluoropyridin-2-yl}ethyl]acetamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: phosphorus(V) oxybromide / N,N-dimethyl-formamide; toluene / 16 h / 90 °C

2.1: propiononitrile / 17 h / 90 °C

3.1: tetrabutyl ammonium fluoride; sulfuric acid / N,N-dimethyl-formamide / 1 h / -40 °C

3.2: -40 °C / pH 3

4.1: methylmagnesium chloride / toluene; tetrahydrofuran / 1 h / -10 °C

4.2: 16 h / 25 °C

4.3: 0.5 h

5.1: hydrogen / (1S,1S',2R,2R')-1,1'-di-tert-butyl-(2,2’)-diphospholane; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate / methanol / 4.5 h / 7500.75 Torr / Autoclave; Charcoal presence

6.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dichloromethane; dimethyl sulfoxide / 1.67 h / 90 °C / Inert atmosphere; Sealed tube

7.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dichloromethane / 3 h / 20 - 80 °C / Inert atmosphere; Sealed tube

With sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; methylmagnesium chloride; potassium acetate; potassium carbonate; phosphorus(V) oxybromide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (1S,1S',2R,2R')-1,1'-di-tert-butyl-(2,2’)-diphospholane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; propiononitrile; 7.1: Suzuki Coupling;