trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid

Base Information

• Chemical Name: trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid
• CAS No.: 1350322-89-2
• Molecular Formula: C₂₇H₂₈ClFN₄O₃
• Molecular Weight: 510.996
• Mol file: 1350322-89-2.mol

Synonyms:trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid

Chemical Property of trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid

There total 12 articles about trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid 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-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid (1350322-89-2)

Guidance literature:

Multi-step reaction with 6 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 / 2 h / 90 °C

6.1: water; lithium hydroxide / methanol / 2 h / 20 °C

6.2: pH 2

With potassium fluoride; 18-crown-6 ether; sulfuric acid; water; isopropylmagnesium chloride; potassium carbonate; triethylamine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

ethyl trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate (1350322-90-5) → trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid (1350322-89-2)

Guidance literature:

ethyl trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate; With water; lithium hydroxide; In methanol; at 20 ℃; for 2h;

In dichloromethane; water; pH=2;

Reference yield:

5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid (1350322-89-2)

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 fluoride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 90 °C

5.1: water; lithium hydroxide / methanol / 2 h / 20 °C

5.2: pH 2

With potassium fluoride; boron trifluoride diethyl etherate; water; potassium hydroxide; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; carbon dioxide; water;

upstream raw materials:

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

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

Downstream raw materials:

Trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)-N,N-dimethylcyclohexanecarboxamide