4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

Base Information

Chemical Name:4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile
CAS No.:1350323-56-6
Molecular Formula:C₂₁H₁₇ClFN₅O
Molecular Weight:409.85
Hs Code.:

Synonyms:4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

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Chemical Property of 4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

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Technology Process of 4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

There total 9 articles about 4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile 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:

: 287922-71-8
4-bromo-1-methyl-1H-pyrazole-3-carbonitrile

: 1350322-64-3
3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

: 1350323-56-6
4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

Guidance literature:: With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 100 ℃; for 0.5h; microwave irradiation;

Reference yield:

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1350323-56-6
4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hydroxide / methanol / 12 h / 20 °C

2.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.5 h / -60 °C

2.2: -60 - 45 °C / Inert atmosphere

3.1: ChiralPak IA / carbon dioxide; methanol / Resolution of racemate

4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 32.5 h / 80 °C

5.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.5 h / 100 °C / microwave irradiation

With boron trifluoride diethyl etherate; potassium acetate; potassium carbonate; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; carbon dioxide; water;

Reference yield:

: 202925-07-3
2-chloro-1-fluoro-4-methoxybenzene

: 1350323-56-6
4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tert-butyl methyl ether; hexanes / 3 h / -78 °C

1.2: 0.75 h / -60 °C

2.1: potassium hydroxide / methanol / 12 h / 20 °C

3.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.5 h / -60 °C

3.2: -60 - 45 °C / Inert atmosphere

4.1: ChiralPak IA / carbon dioxide; methanol / Resolution of racemate

5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 32.5 h / 80 °C

6.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.5 h / 100 °C / microwave irradiation

With n-butyllithium; boron trifluoride diethyl etherate; potassium acetate; potassium carbonate; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; tert-butyl methyl ether; carbon dioxide; water;