5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine

Base Information

• Chemical Name: 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine
• CAS No.: 1359945-12-2
• Molecular Formula: C₂₄H₁₉BrClN₃
• Molecular Weight: 464.792

Synonyms:5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine

Chemical Property of 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine

Chemical Property:

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Technology Process of 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine

There total 4 articles about 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine 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: 77.0%

2-[2-methyl-4-(4-chloro-pyridin-3-yl)phenyl]-4,4,5,5-tetramethyl-1,3-dioxaborolane (1359945-08-6) + 2-methyl-4-bromoiodobenzene (116632-39-4) → 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine (1359945-12-2) + 5'-[2-methyl-4-(6-chloro-pyridin-3-yl)phenyl]-3',5-dimethyl-6-[2-methyl-4-(6-chloro-pyridin-3-yl)phenyl]-3,2'-bipyridine (1359945-16-6)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; for 20h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.12.074

Reference yield:

1-bromo-4-iodo-2-methylbenzene (202865-85-8) → 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine (1359945-12-2) + 5'-[2-methyl-4-(6-chloro-pyridin-3-yl)phenyl]-3',5-dimethyl-6-[2-methyl-4-(6-chloro-pyridin-3-yl)phenyl]-3,2'-bipyridine (1359945-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 24 h / Inert atmosphere; Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 16 h / Reflux; Inert atmosphere

3: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 20 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; sodium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; water; 1: Suzuki-Miyaura coupling / 3: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2011.12.074

Reference yield:

6-chloropyridin-3-ylboronic acid (444120-91-6) → 5′-bromo-3′,5-dimethyl-6-(2-methyl-4-(4-chloropyridin-3-yl)phenyl)-3,2′-bipyridine (1359945-12-2) + 5'-[2-methyl-4-(6-chloro-pyridin-3-yl)phenyl]-3',5-dimethyl-6-[2-methyl-4-(6-chloro-pyridin-3-yl)phenyl]-3,2'-bipyridine (1359945-16-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water / 24 h / Inert atmosphere; Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 16 h / Reflux; Inert atmosphere

3: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 20 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; sodium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; water; 1: Suzuki-Miyaura coupling / 3: Suzuki-Miyaura coupling;

DOI:10.1016/j.tet.2011.12.074

upstream raw materials:

2-[2-methyl-4-(4-chloro-pyridin-3-yl)phenyl]-4,4,5,5-tetramethyl-1,3-dioxaborolane

2-methyl-4-bromoiodobenzene

2-chloro-5-(4-bromo-3-methylphenyl)pyridine

1-bromo-4-iodo-2-methylbenzene

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