3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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Chemical Name:3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine
CAS No.:1350323-87-3
Molecular Formula:C₂₁H₂₀ClFN₄O₂
Molecular Weight:414.867
Hs Code.:

Synonyms:3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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Chemical Property of 3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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Technology Process of 3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

There total 8 articles about 3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine 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:

: 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

: 89717-68-0
4-bromo-5-methoxy-1-methylpyrazole

: 1350323-87-3
3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Guidance literature:: With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; water; at 100 ℃; for 0.5h; Inert atmosphere; microwave irradiation;

Reference yield:

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

: 1350323-87-3
3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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 / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere; microwave irradiation

With boron trifluoride diethyl etherate; potassium acetate; potassium carbonate; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; methanol; carbon dioxide; water;

Reference yield:

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

: 1350323-87-3
3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(5-methoxy-1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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 / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere; microwave irradiation

With n-butyllithium; boron trifluoride diethyl etherate; potassium acetate; potassium carbonate; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; tert-butyl methyl ether; carbon dioxide; water;