5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline

Base Information

• Chemical Name: 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline
• CAS No.: 1615223-19-2
• Molecular Formula: C₂₇H₃₀N₄O₄
• Molecular Weight: 474.56

Synonyms:5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline

Chemical Property of 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline

Chemical Property:

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Technology Process of 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline

There total 4 articles about 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline 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: 30.0%

5-bromo-2-(2-morpholinoethoxy)benzenamine (946786-56-7) + 3-(3,4-dimethoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1615223-35-2) → 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline (1615223-19-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; In 1,4-dioxane; water; at 100 ℃; Inert atmosphere;

DOI:10.1039/c4ob00053f

Reference yield:

5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (757978-19-1) → 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline (1615223-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube

2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 12 h / 90 °C / Inert atmosphere

4: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; caesium carbonate; potassium hydroxide; In 1,4-dioxane; methanol; water; 1: |Suzuki Coupling / 4: |Suzuki Coupling;

DOI:10.1039/c4ob00053f

Reference yield:

3,4-Dimethoxyphenylboronic acid (122775-35-3) → 5-(3-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-morpholinoethoxy)aniline (1615223-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube

2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 12 h / 90 °C / Inert atmosphere

4: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; caesium carbonate; potassium hydroxide; In 1,4-dioxane; methanol; water; 1: |Suzuki Coupling / 4: |Suzuki Coupling;

DOI:10.1039/c4ob00053f

upstream raw materials:

5-bromo-2-(2-morpholinoethoxy)benzenamine

3-(3,4-dimethoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

3,4-Dimethoxyphenylboronic acid

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