4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Base Information

• Chemical Name: 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide
• CAS No.: 1070889-90-5
• Molecular Formula: C₂₁H₁₆ClN₃O₂
• Molecular Weight: 377.83
• Mol file: 1070889-90-5.mol

Synonyms:4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Chemical Property of 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide

There total 9 articles about 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-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:

2-amino-5-bromo-4-methylpyridine (98198-48-2) → 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide (1070889-90-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen bromide; bromine; sodium nitrite / water / 1 h / 0 - 5 °C

1.2: 20 °C / pH ~ 13

2.1: n-butyllithium / toluene; pentane / 2 h / -78 °C

2.2: 1 h / -78 °C

2.3: -10 °C

3.1: trichlorophosphate / toluene / 5 h / Heating / reflux

4.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 12 h / 95 °C

With n-butyllithium; hydrogen bromide; bromine; potassium carbonate; sodium nitrite; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; toluene; pentane;

Reference yield:

5-bromo-4-methyl-pyridine-2-carbonitrile (886364-86-9) + 4-chloro-N-(2-hydroxy-phenyl)-N-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1070892-31-7) → 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide (1070889-90-5)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 95 ℃; for 12h;

Reference yield:

3-bromo-4-chlorobenzoic acid (42860-10-6) → 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide (1070889-90-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h

2.1: sodium hydrogencarbonate / water; acetonitrile / 1.5 h

2.2: 16 h / 20 °C

3.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 95 °C

4.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 12 h / 95 °C

With oxalyl dichloride; potassium acetate; sodium hydrogencarbonate; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-dimethyl-formamide; In 1,4-dioxane; dichloromethane; water; acetonitrile;

upstream raw materials:

5-bromo-4-methyl-pyridine-2-carbonitrile

4-chloro-N-(2-hydroxy-phenyl)-N-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

2-amino-5-bromo-4-methylpyridine

2,5-Dibromo-4-methylpyridine

Downstream raw materials:

4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide

3-(2-{[4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid