1-{cis-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]cyclohexyl}-L-proline

Base Information

• Chemical Name: 1-{cis-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]cyclohexyl}-L-proline
• CAS No.: 1350324-66-1
• Molecular Formula: C₃₁H₃₃ClF₃N₅O₃
• Molecular Weight: 616.083
• Mol file: 1350324-66-1.mol

Synonyms:1-{cis-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]cyclohexyl}-L-proline

Chemical Property of 1-{cis-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]cyclohexyl}-L-proline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{cis-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]cyclohexyl}-L-proline

There total 15 articles about 1-{cis-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]cyclohexyl}-L-proline 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:

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]cyclohexanone (1350324-62-7) + methyl (2S)-pyrrolidine carboxylate (2577-48-2) → 1-{trans-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]cyclohexyl}-L-proline (1350324-65-0) + 1-{cis-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]cyclohexyl}-L-proline (1350324-66-1)

Guidance literature:

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]cyclohexanone; methyl (2S)-pyrrolidine carboxylate; With sodium tris(acetoxy)borohydride; triethylamine; In 1,2-dichloro-ethane; at 50 ℃;

With lithium hydroxide monohydrate; In methanol; at 50 ℃; for 3h;

Reference yield:

tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1350324-11-6) → 1-{trans-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]cyclohexyl}-L-proline (1350324-65-0) + 1-{cis-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]cyclohexyl}-L-proline (1350324-66-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 95 °C

2.1: hydrogenchloride; water / 1,4-dioxane / 45 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.08 h / 20 °C

4.1: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 50 °C

4.2: 3 h / 50 °C

With hydrogenchloride; water; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane;

Reference yield:

tert-butyl 5-bromo-3-[(1S)-1-{6-[(tert-butoxycarbonyl)oxy]-2-chloro-3-fluorophenyl}ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1350324-14-9) → 1-{trans-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]cyclohexyl}-L-proline (1350324-65-0) + 1-{cis-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]cyclohexyl}-L-proline (1350324-66-1)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 95 °C

4.1: hydrogenchloride; water / 1,4-dioxane / 45 °C

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.08 h / 20 °C

6.1: triethylamine; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 50 °C

6.2: 3 h / 50 °C

With piperidine; hydrogenchloride; water; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

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]cyclohexanone

methyl (2S)-pyrrolidine carboxylate

toluene-4-sulfonic acid 1,4-dioxa-spiro[4.5]dec-8-yl ester

5-bromo-1H-pyrrolo[2,3-b]pyridine