1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

Base Information

Chemical Name:1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone
CAS No.:1350324-91-2
Molecular Formula:C₂₇H₂₇ClF₃N₅O₂
Molecular Weight:545.992
Hs Code.:

1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

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Chemical Property of 1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

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Technology Process of 1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

There total 14 articles about 1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone 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:

: 1350322-47-2
5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

: 1350324-91-2
1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: boron tribromide / dichloromethane / 18.16 h / -78 - 20 °C

1.2: 0.5 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -40 - -10 °C

2.2: 17 h / -40 - 20 °C

3.1: piperidine / dichloromethane / 16 h / 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C / sealed tube

5.1: potassium fluoride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.5 h / 100 °C / microwave irradiation

6.1: hydrogenchloride; water / 1,4-dioxane / 30 °C

7.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0.17 h / 20 °C

With piperidine; hydrogenchloride; potassium fluoride; water; boron tribromide; sodium hydride; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

: 1350322-46-1
5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

: 1350324-91-2
1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: boron tribromide / dichloromethane / 18.16 h / -78 - 20 °C

2.2: 0.5 h / 0 - 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -40 - -10 °C

3.2: 17 h / -40 - 20 °C

4.1: piperidine / dichloromethane / 16 h / 20 °C

5.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C / sealed tube

6.1: potassium fluoride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.5 h / 100 °C / microwave irradiation

7.1: hydrogenchloride; water / 1,4-dioxane / 30 °C

8.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0.17 h / 20 °C

With piperidine; hydrogenchloride; potassium fluoride; water; boron tribromide; sodium hydride; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; carbon dioxide; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

: 1350322-49-4
5-bromo-3-[(2-chloro-3-fluoro-6-methoxyphenyl)-hydroxymethyl]-1H-pyrrolo[2,3-b]pyridine

: 1350324-91-2
1-{4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]piperidin-1-yl}ethanone

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: -60 - 45 °C / Inert atmosphere

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

3.1: boron tribromide / dichloromethane / 18.16 h / -78 - 20 °C

3.2: 0.5 h / 0 - 20 °C

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -40 - -10 °C

4.2: 17 h / -40 - 20 °C

5.1: piperidine / dichloromethane / 16 h / 20 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C / sealed tube

7.1: potassium fluoride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.5 h / 100 °C / microwave irradiation

8.1: hydrogenchloride; water / 1,4-dioxane / 30 °C

9.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 0.17 h / 20 °C

With piperidine; hydrogenchloride; potassium fluoride; boron trifluoride diethyl etherate; water; boron tribromide; sodium hydride; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; carbon dioxide; water; N,N-dimethyl-formamide; mineral oil;