133791-17-0

Usage

Uses

Used in Chemical Research:
Methyl [E]-2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate is used as a reference standard in chemical research for its unique structural properties, aiding in the identification and analysis of similar compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, Methyl [E]-2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate is utilized in the development of new drugs, leveraging its complex structure to explore its potential biological activities and therapeutic applications.
Used in Drug Development:
Methyl [E]-2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate is employed in drug development processes to investigate its potential as a lead compound for the creation of novel pharmaceuticals, given its unique molecular composition and the possibility of specific biological interactions.
Used in the Scientific Community:
For the scientific community, Methyl [E]-2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate serves as a subject of interest for further exploration, potentially leading to new discoveries in various fields due to its complex and potentially active molecular structure.

InChI:InChI=1/C28H22ClNO3/c1-33-28(32)25-8-3-2-6-20(25)12-16-27(31)22-7-4-5-19(17-22)9-14-24-15-11-21-10-13-23(29)18-26(21)30-24/h2-11,13-15,17-18H,12,16H2,1H3

Synthetic route

C17H11BrClN + methyl 2-(3-oxopropane)benzoate (106515-77-9) → 2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0)

Conditions	Yield
With pyrrolidine; tris-(dibenzylideneacetone)dipalladium(0); 2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole In N,N-dimethyl acetamide at 140℃; for 4h; Solvent; Reagent/catalyst; Molecular sieve; Inert atmosphere;	75%

o-iodo-methyl-benzoic acid (610-97-9) + 1‐[3‐(2‐(7-chloro‐2‐quinolinyl)vinyl)phenyl]‐2-propen-1-ol → 2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0)

Conditions	Yield
Stage #1: o-iodo-methyl-benzoic acid; 1‐[3‐(2‐(7-chloro‐2‐quinolinyl)vinyl)phenyl]‐2-propen-1-ol With triethylamine In butan-1-ol at 96℃; for 8h; Stage #2: With sodium formate In butan-1-ol at 75℃; Stage #3: In water at 55℃; for 1h;

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) → 2-[(3S)-3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoic acid methyl ester (142569-69-5)

Conditions	Yield
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction;	99%
Stage #1: 2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 10℃; for 2.66667h; Stage #2: With hydrogenchloride In water at 20℃;	68.8%
With [iridium(dihydride)(chloride)((3,5-(tBu)2-C6H3)2P)(C17H10)NHCHC5H3N(CH3)]; potassium tert-butylate; hydrogen In methanol at 50℃; under 22502.3 - 24002.4 Torr; for 15h; Reagent/catalyst; Solvent; Pressure;	n/a

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) → -2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester (150026-72-5)

Conditions	Yield
With sodium formate; [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; Aliquat 336 In dichloromethane; water at 40℃; for 60h; Product distribution / selectivity; Inert atmosphere;	89%

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) → C27H18ClNO2

Conditions	Yield
With potassium tert-butylate In ethanol at 0℃; for 24h;	85%

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) → C27H20ClNO2

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate; C52H67ClIrN2P; hydrogen / 20 - 30 °C / 15001.5 - 16501.7 Torr / Autoclave; Schlenk technique; Inert atmosphere 1.2: 0 - 50 °C 2.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 25 °C View Scheme

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) → C29H28ClNO3

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium tert-butylate; C52H67ClIrN2P; hydrogen / 20 - 30 °C / 15001.5 - 16501.7 Torr / Autoclave; Schlenk technique; Inert atmosphere; Large scale 2: hydrogen / tetrahydrofuran / 25 - 35 °C / 4500.45 - 6000.6 Torr / Autoclave 3: potassium tert-butylate / 3 h / 50 °C View Scheme

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) + ethanol (64-17-5) → C27H22ClNO3

Conditions	Yield
Stage #1: 2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester; ethanol With C52H67ClIrN2P; potassium tert-butylate; hydrogen at 20 - 30℃; under 15001.5 - 16501.7 Torr; Autoclave; Schlenk technique; Inert atmosphere; Stage #2: With water; sodium hydroxide In methanol at 0 - 50℃;	7.8 g

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) + ethanol (64-17-5) → 2-[(3S)-3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoic acid methyl ester (142569-69-5) + C27H20ClNO2 + C29H26ClNO3

Conditions	Yield
With C52H67ClIrN2P; hydrogen In dichloromethane at 30℃; under 11400.8 Torr; for 0.5h; enantioselective reaction;	A n/a B n/a C n/a

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) + ethanol (64-17-5) → 2-[(3S)-3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoic acid methyl ester (142569-69-5) + C29H26ClNO3

Conditions	Yield
With C52H67ClIrN2P; potassium tert-butylate; hydrogen at 20 - 30℃; under 15001.5 - 16501.7 Torr; Autoclave; Schlenk technique; Inert atmosphere; Large scale; Overall yield = 94 %; Overall yield = 29.6 kg; enantioselective reaction;	A n/a B n/a

2-(3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-oxopropyl)benzoic acid methyl ester (133791-17-0) + ethanol (64-17-5) → C28H26ClNO3 + 2-[(3S)-3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoic acid methyl ester (142569-69-5) + C29H26ClNO3 + C29H28ClNO3

Conditions	Yield
With C52H67ClIrN2P; hydrogen at 70℃; under 11400.8 Torr; for 0.5h; enantioselective reaction;	A n/a B n/a C n/a D n/a

Upstream product

• 106515-77-9 methyl 2-(3-oxopropane)benzoate 
• 610-97-9 o-iodo-methyl-benzoic acid 

Downstream Products

• 142569-69-5 2-[(3S)-3-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoic acid methyl ester 
• 150026-72-5 -2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis method of montelukast sodium intermediate

The invention provides a synthesis method of a montelukast sodium intermediate. The synthesis method comprises the following steps: (1) carrying out Witting reaction on a compound (IV) and 3-bromobenzyl bromide to obtain a compound (II); and (2) carrying out a coupling reaction on the compound (II) and a compound (III) under the action of a palladium catalyst to obtain the compound (I). The synthesis method is short in step, mild in condition, easyand convenient to operate, beneficial to reducing the process cost and capable of realizing industrial production.