trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol

Base Information

• Chemical Name: trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol
• CAS No.: 1350425-14-7
• Molecular Formula: C₂₆H₂₆ClF₃N₄O₂
• Molecular Weight: 521.942

Synonyms:trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol

Chemical Property of trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol

Chemical Property:

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Technology Process of trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol

There total 14 articles about trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol 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:

C37H45(2)H3ClF3N4O4Si → trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H3)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol (1350425-14-7)

Guidance literature:

C₃₇H₄₅⁽²⁾H₃ClF₃N₄O₄Si; With hydrogenchloride; water; In 1,4-dioxane; at 20 ℃; for 12h;

With sodium hydrogencarbonate; In dichloromethane; water;

Reference yield:

5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H3)ethyl]-1H-pyrrolo[2,3-b]pyridine (1350325-19-7) → trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H3)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol (1350425-14-7)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 0 °C

2.1: sodium hydride / tetrahydrofuran / 0 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 70 °C

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

5.1: hydrogenchloride; water / 1,4-dioxane / 12 h / 20 °C

With hydrogenchloride; water; boron tribromide; sodium hydride; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H3)ethyl]-1H-pyrrolo[2,3-b]pyridine (1350325-20-0) → trans-4-(4-{3-[(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl](2,2,2-2H3)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanol (1350425-14-7)

Guidance literature:

Multi-step reaction with 6 steps

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

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

2.2: 0 °C

3.1: sodium hydride / tetrahydrofuran / 0 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 70 °C

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

6.1: hydrogenchloride; water / 1,4-dioxane / 12 h / 20 °C

With hydrogenchloride; water; boron tribromide; sodium hydride; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; carbon dioxide; water; N,N-dimethyl-formamide;

upstream raw materials:

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

4-iodo-1-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-pyrazole

4-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

1-(trans-4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-1H-pyrazole

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