4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile

Base Information

• Chemical Name: 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile
• CAS No.: 1415387-42-6
• Molecular Formula: C₂₇H₂₄BrN₅O
• Molecular Weight: 514.424

Synonyms:4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile

Chemical Property of 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile

Chemical Property:

Purity/Quality:

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Technology Process of 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile

There total 13 articles about 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile 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:

1,4-bromoiodobenzene (589-87-7) → 4-(1-(5-(4-(azetidin-1-yl)-3H-imidazo[4,5-c]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (1399176-99-8) + C21H20N2O2 + 4-(1-(2,4-dimethyl-5-(6-(methylsulfonyl)-3H-imidazo[4,5-b]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile (1399176-08-9) + 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile (1415387-42-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

3.1: trichlorophosphate / pyridine / 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C

5.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; palladium 10% on activated carbon; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; pyridine; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ml300335r

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 4-(1-(5-(4-(azetidin-1-yl)-3H-imidazo[4,5-c]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (1399176-99-8) + C21H20N2O2 + 4-(1-(2,4-dimethyl-5-(6-(methylsulfonyl)-3H-imidazo[4,5-b]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile (1399176-08-9) + 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile (1415387-42-6) + 4-(1-(2,4-dimethyl-5-(6-(methylsulfonyl)-3H-imidazo[4,5-c]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile (1399176-07-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

3.1: trichlorophosphate / pyridine / 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C

5.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; palladium 10% on activated carbon; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; pyridine; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ml300335r

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 4-(1-(5-(4-(azetidin-1-yl)-3H-imidazo[4,5-c]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (1399176-99-8) + C21H20N2O2 + 4-(1-(2,4-dimethyl-5-(6-(methylsulfonyl)-3H-imidazo[4,5-b]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile (1399176-08-9) + 4-(1-(5-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethyllbenzoyl)piperidin-4-yl)benzonitrile (1415387-42-6) + 4-(1-(2,4-dimethyl-5-(6-(methylsulfonyl)-3H-imidazo[4,5-c]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile (1399176-07-8) + 4-(1-(5-(5-(azetidin-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl)-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile (1399176-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(l) chloride; potassium hydroxide; 1,10-Phenanthroline

2: potassium iodide; potassium iodate / acetic acid

3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide

With bis-triphenylphosphine-palladium(II) chloride; potassium iodate; copper(l) iodide; 1,10-Phenanthroline; potassium iodide; copper(l) chloride; potassium hydroxide; In acetic acid;

DOI:10.1016/j.dyepig.2013.12.016

upstream raw materials:

5-iodo-2,4-dimethylbenzoic acid

5-bromo-pyridine-2,3-diamine

4-(1-(5-formyl-2,4-dimethylbenzoyl)piperidin-4-yl)benzonitrile

1,4-bromoiodobenzene

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