racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 1350325-20-0
• Molecular Formula: C₁₆H₁₃BrClFN₂O
• Molecular Weight: 386.624

Synonyms:racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine

Chemical Property of racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine

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Technology Process of racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine

There total 1 articles about racemic 5-bromo-3-[1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine 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:

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→ 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)

Guidance literature:

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) → 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) + 5-bromo-3-[(1R)-1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H3)ethyl]-1H-pyrrolo[2,3-b]pyridine

Guidance literature:

With ChiralPak IA; In methanol; carbon dioxide; Resolution of racemate;

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 hydrochloride

Guidance literature:

Multi-step reaction with 7 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

7.1: hydrogenchloride / diethyl ether; methanol / 20 °C

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

Downstream raw materials:

5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)(2,2,2-2H₃)ethyl]-1H-pyrrolo[2,3-b]pyridine

2-[(1S)-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2,2,2-2H₃)ethyl]-3-chloro-4-fluorophenol

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

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

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