3-Cyano-4-phenyl-6-(3-bromo-6-hydroxy)phenyl-2(1H)-pyridone

Base Information

• Chemical Name: 3-Cyano-4-phenyl-6-(3-bromo-6-hydroxy)phenyl-2(1H)-pyridone
• CAS No.: 491871-58-0
• Molecular Formula: C18H11BrN2O2
• Molecular Weight: 367.19614
• Mol file: 491871-58-0.mol

Synonyms:3-Cyano-4-phenyl-6-(3-bromo-6-hydroxy)phenyl-2(1H)-pyridone;TCS PIM-1 1;SC 204330;6-(5-Bromo-2-hydroxyphenyl)-1,2-dihydro-2-oxo-4-phenyl-3-pyridinecarbonitrile;TCS PIM-1;TCS PIM-1 1, >=98%

Chemical Property of 3-Cyano-4-phenyl-6-(3-bromo-6-hydroxy)phenyl-2(1H)-pyridone

Chemical Property:

• Boiling Point: 592.6±50.0 °C(Predicted)
• PKA: 6.93±0.10(Predicted)
• Density: 1.63±0.1 g/cm3(Predicted)
• Storage Temp.: Store at +4°C
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥12.8 mg/mL in DMSO

Purity/Quality:

97% ^*data from raw suppliers

TCS PIM-1 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: TCS PIM-1 1 is a Pim-1 kinase inhibitor.

Technology Process of 3-Cyano-4-phenyl-6-(3-bromo-6-hydroxy)phenyl-2(1H)-pyridone

There total 1 articles about 3-Cyano-4-phenyl-6-(3-bromo-6-hydroxy)phenyl-2(1H)-pyridone 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-(5-bromo-2-hydroxyphenyl)-3-phenyl-1,3-propanedione (5067-24-3) + cyanoacetic acid amide (107-91-5) → 6-(5-bromo-2-hydroxyphenyl)-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile (491871-58-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 90 ℃; for 16h;

DOI:10.1016/j.bmcl.2006.12.086

Reference yield: 16.0%

6-(5-bromo-2-hydroxyphenyl)-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile (491871-58-0) → 6-(5-bromo-2-hydroxy-phenyl)-2-chloro-4-phenyl-nicotinonitrile (935290-58-7)

Guidance literature:

With pyridine; trichlorophosphate; In 1,4-dioxane; at 80 ℃; for 14h;

DOI:10.1016/j.bmcl.2006.12.086

Reference yield:

6-(5-bromo-2-hydroxyphenyl)-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile (491871-58-0) → 6-(5-bromo-2-hydroxy-phenyl)-2-hydrazino-4-phenyl-nicotinonitrile (935290-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 16 percent / POCl₃; pyridine / dioxane / 14 h / 80 °C

2: 90 percent / hydrazine / dimethylformamide; H₂O / 14 h / 90 °C

With pyridine; hydrazine; trichlorophosphate; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.12.086

upstream raw materials:

1-(5-bromo-2-hydroxyphenyl)-3-phenyl-1,3-propanedione

cyanoacetic acid amide

Downstream raw materials:

6-(5-bromo-2-hydroxy-phenyl)-2-chloro-4-phenyl-nicotinonitrile

6-(5-bromo-2-hydroxy-phenyl)-2-hydrazino-4-phenyl-nicotinonitrile