N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

Base Information

Chemical Name:N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide
CAS No.:1351477-32-1
Molecular Formula:C₂₇H₂₉N₅O
Molecular Weight:439.56
Hs Code.:

Synonyms:N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

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Chemical Property of N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

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Technology Process of N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

There total 7 articles about N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide 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: 20.0%

: 832695-88-2
3-(methylcarbamoyl)phenylboronic acid

: 1351477-60-5
3-iodo-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

: 1351477-32-1
N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

Guidance literature:: 3-(methylcarbamoyl)phenylboronic acid; 3-iodo-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 70 ℃; for 8h; Inert atmosphere;

With potassium carbonate; In methanol; water; at 60 ℃; for 6h;
DOI:10.1016/j.bmcl.2020.127749

Reference yield:

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1351477-32-1
N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 80 °C / Inert atmosphere

2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

3.2: 1 h / 0 - 20 °C

4.1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 18 h / 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 8 h / 70 °C / Inert atmosphere

5.2: 6 h / 60 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium tris(acetoxy)borohydride; sodium hydride; sodium carbonate; potassium carbonate; acetic acid; In 1,4-dioxane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2020.127749

Reference yield:

: 87199-17-5
4-formylphenylboronic acid,

: 1351477-32-1
N-methyl-3-{5-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}benzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 80 °C / Inert atmosphere

2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

3.2: 1 h / 0 - 20 °C

4.1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 18 h / 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane; water / 8 h / 70 °C / Inert atmosphere

5.2: 6 h / 60 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium tris(acetoxy)borohydride; sodium hydride; sodium carbonate; potassium carbonate; acetic acid; In 1,4-dioxane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2020.127749