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]cyclohexanecarboxamide

Base Information

• Chemical Name: 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]cyclohexanecarboxamide
• CAS No.: 1350324-33-2
• Molecular Formula: C₂₇H₂₇ClF₃N₅O₂
• Molecular Weight: 545.992
• Mol file: 1350324-33-2.mol

Synonyms: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]cyclohexanecarboxamide

Chemical Property of 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]cyclohexanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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]cyclohexanecarboxamide

There total 19 articles about 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]cyclohexanecarboxamide 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:

cis-4-hydroxycyclohexanecarboxylic acid (3685-26-5,17419-81-7,3685-22-1) → 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]cyclohexanecarboxamide (1350324-33-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sulfuric acid / 2 h / 70 °C

2.1: triethylamine / dichloromethane / 25 °C

3.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 80 °C

4.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 20 °C

4.2: 2 h / 20 °C

5.1: potassium fluoride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 0.5 h / 95 °C / microwave irradiation

6.1: hydrogenchloride; water / methanol / 1 h / 45 °C

7.1: water; lithium hydroxide monohydrate / 2 h / 40 °C / pH 12

7.2: pH 6

8.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ammonium chloride / dichloromethane / 0.33 h / 20 °C

With hydrogenchloride; potassium fluoride; 18-crown-6 ether; lithium hydroxide monohydrate; sulfuric acid; water; isopropylmagnesium chloride; potassium carbonate; ammonium chloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

C27H26ClF3N4O3 → 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]cyclohexanecarboxamide (1350324-33-2)

Guidance literature:

With ammonium chloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.333333h;

Reference yield:

5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine (1350322-47-2) → 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]cyclohexanecarboxamide (1350324-33-2)

Guidance literature:

Multi-step reaction with 8 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 / 95 °C / microwave irradiation

6.1: hydrogenchloride; water / methanol / 1 h / 45 °C

7.1: water; lithium hydroxide monohydrate / 2 h / 40 °C / pH 12

7.2: pH 6

8.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ammonium chloride / dichloromethane / 0.33 h / 20 °C

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

upstream raw materials:

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

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

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

2-chloro-3-fluoro-6-methoxy-benzaldehyde