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

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-carboxamide
CAS No.:1350323-46-4
Molecular Formula:C₂₁H₁₉ClFN₅O₂
Molecular Weight:427.866
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-carboxamide

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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-carboxamide

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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-carboxamide

There total 8 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-carboxamide 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:

: 384812-85-5
4-bromo-1-methyl-1H-pyrazole-3-carboxamide

: 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

: 1350323-46-4
4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carboxamide

Guidance literature:: With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 95 ℃; for 0.5h;

Reference yield:

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

: 1350323-46-4
4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carboxamide

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 / 95 °C

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

: 1350323-46-4
4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carboxamide

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 / 95 °C

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;