1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]-1-propanone

Base Information

• Chemical Name: 1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]-1-propanone
• CAS No.: 1258428-71-5
• Molecular Formula: C₂₉H₂₆ClNO₂
• Molecular Weight: 455.984
• Mol file: 1258428-71-5.mol

Synonyms:1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]-1-propanone;Montelukast Related Impuirty 1

Chemical Property of 1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]-1-propanone

Chemical Property:

• Boiling Point: 651.5±55.0 °C(Predicted)
• PKA: 14.46±0.29(Predicted)
• Density: 1.237±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

99%min. ^*data from raw suppliers

1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]-1-propanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]-1-propanone is an impurity of Montelukast (M568000), a selective leukotriene D4-receptor antagonist that is used as an antiasthmatic.

Technology Process of 1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]-1-propanone

There total 23 articles about 1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]-1-propanone 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: 89.0%

7-chloro-2-ethenylquinoline (177748-00-4) + 1-(3-bromophenyl)-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one (762272-97-9) → trans-1-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one (1258428-71-5)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100 ℃; for 5.5h; Inert atmosphere;

Reference yield: 82.0%

2-(2-bromophenyl)propanol (7073-69-0) + (E)-3-<2-(7-chloro-2-quinolinyl)ethenyl>-α-ethenylphenylmethanol (149968-10-5) → trans-1-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one (1258428-71-5)

Guidance literature:

2-(2-bromophenyl)propanol; (E)-3-<2-(7-chloro-2-quinolinyl)ethenyl>-α-ethenylphenylmethanol; With trans dibromo diammine palladium (II); N-Methyldicyclohexylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100 ℃; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 120 ℃; for 6h; Solvent; Temperature; Inert atmosphere;

Reference yield: 80.0%

(E)-2-(2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-oxopropyl)phenyl)propan-2-yl acetate → trans-1-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one (1258428-71-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; at 20 - 45 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.5b00197

upstream raw materials:

2-{2-[2-(2-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}[1,3]dioxolan-2-yl)ethyl]phenyl}propan-2-ol

2-(2-bromophenyl)propanol

(E)-3-<2-(7-chloro-2-quinolinyl)ethenyl>-α-ethenylphenylmethanol

2-((2-(2-bromophenyl)propan-2-yl)oxy)tetrahydro-2H-pyran

Downstream raw materials:

(S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-methyl-1-trimethylsilanyloxy-ethyl)-phenyl]-propan-1-ol

C₃₃H₃₈ClNO₄SSi

(1-{(R)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)vinyl]phenyl}-3-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]propylsulfanylmethyl}cyclopropyl)acetic acid methyl ester

Refernces

• 1、 -. "For the synthesis of montelukast intermediate compound and its preparation method". . . Retrieved 2017/04/12.
• 2、 -. "PROCESS FOR THE PREPARATION OF MONTELUKAST SODIUM". Page/Page column 14-15. . Retrieved 2012/03/09.