N₁-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine

Base Information

• Chemical Name: N₁-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine
• CAS No.: 1020206-18-1
• Molecular Formula: C₁₈H₂₂BrClN₄O
• Molecular Weight: 425.756

Synonyms:N₁-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine

Chemical Property of N₁-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine

Chemical Property:

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Technology Process of N₁-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine

There total 5 articles about N₁-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine 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: 52.0%

3-bromo-5-chloro-N-(2-((1-methylpiperidin-4-yl)methoxy)-5-nitrophenyl)pyridin-2-amine (1020206-17-0) → N1-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine (1020206-18-1)

Guidance literature:

With triphenyl phosphite; ammonium metavanadate; hydrogen; platinum on carbon;

Reference yield:

1-methyl-4-piperidinemethanol (20691-89-8) → N1-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine (1020206-18-1)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / dimethyl sulfoxide / 20 - 40 °C / Inert atmosphere

2: sodium iodate; iodine / sulfuric acid / 30 °C

3: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 20 - 100 °C / Inert atmosphere

4: triphenyl phosphite; ammonium metavanadate; hydrogen / platinum on carbon

With triphenyl phosphite; ammonium metavanadate; sodium iodate; hydrogen; iodine; sodium hydride; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; platinum on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; sulfuric acid; dimethyl sulfoxide;

Reference yield:

1-methyl-4-[(4-nitrophenoxy)methyl]piperidine (902454-25-5) → N1-(3-bromo-5-chloropyridin-2-yl)-6-((1-methylpiperidin-4-yl)methoxy)benzene-1,3-diamine (1020206-18-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium iodate; iodine / sulfuric acid / 30 °C

2: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 20 - 100 °C / Inert atmosphere

3: triphenyl phosphite; ammonium metavanadate; hydrogen / platinum on carbon

With triphenyl phosphite; ammonium metavanadate; sodium iodate; hydrogen; iodine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; platinum on carbon; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; sulfuric acid;

upstream raw materials:

3-bromo-5-chloro-N-(2-((1-methylpiperidin-4-yl)methoxy)-5-nitrophenyl)pyridin-2-amine

1-methyl-4-[(4-nitrophenoxy)methyl]piperidine

1-methyl-4-piperidinemethanol

4-((2-iodo-4-nitrophenoxy)methyl)-1-methylpiperidine

Downstream raw materials:

3-(3-chloro-8-((1-methylpiperidin-4-yl)methoxy)-9H-pyrido[2,3-b]indol-5-yl)-N-cyclopropylbenzamide

3-chloro-N-(3-methyl-4-(4-methylpiperazin-1-yl)phenyl)-8-((1-methylpiperidin-4-yl)methoxy)-9H-pyrido[2,3-b]indol-5-amine

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