3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

Base Information

Chemical Name:3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile
CAS No.:1155846-65-3
Molecular Formula:C₂₀H₁₄ClN₅O₂
Molecular Weight:391.816
Hs Code.:

Synonyms:3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

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Chemical Property of 3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

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Technology Process of 3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

There total 10 articles about 3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]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:

: 1155847-60-1
3-(3-bromo-5-chlorophenoxy)-4-methyl-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)pyridin-2(1H)-one

: 557-21-1
dicyanozinc

: 1155846-65-3
3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

Guidance literature:: tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 20.3333h;

Reference yield:

: 884494-37-5
2-bromo-3-fluoro-4-methylpyridine

: 1155846-65-3
3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

Guidance literature:: Multi-step reaction with 9 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 2 h / 100 °C

2: potassium carbonate / N,N-dimethyl-formamide / 0.33 h / 55 °C

3: hydrogenchloride; water / 2 h / 100 °C

4: pyridine; diphenyl phosphoryl azide; triethylamine / 1 h / 65 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 1 h / 90 °C

6: trifluoroacetic acid

7: sulfuric acid; sodium nitrite

8: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C

9: trifluoroacetic acid

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; diphenyl phosphoryl azide; water; potassium carbonate; triethylamine; trifluoroacetic acid; sodium nitrite; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; 4: Curtius rearrangement;
DOI:10.1016/j.bmcl.2011.10.027

Reference yield:

: 1034709-24-4
3-(3-bromo-5-chlorophenoxy)-4-methylpyridine-2-carboxylic acid

: 1155846-65-3
3-chloro-5-{[4-methyl-2-oxo-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1,2-dihydropyridin-3-yl]oxy}benzonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine; diphenyl phosphoryl azide; triethylamine / 1 h / 65 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1-methyl-pyrrolidin-2-one / 1 h / 90 °C

3: trifluoroacetic acid

4: sulfuric acid; sodium nitrite

5: potassium carbonate / N,N-dimethyl-formamide / 2 h / 55 °C

6: trifluoroacetic acid

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; diphenyl phosphoryl azide; potassium carbonate; triethylamine; trifluoroacetic acid; sodium nitrite; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; 1: Curtius rearrangement;
DOI:10.1016/j.bmcl.2011.10.027