154057-56-4

Basic information

• Product Name: 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline
• Synonyms: 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline;Quinoline,3-(broMoMethyl)-2-cyclopropyl-4-(4-fluoropenyl);3-(broMoMethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline 3-(broMoMethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline;2-CYCLOPROPYL-3-(BROMOMETHYL)-4-(4-FLUOROPHENYL)-QUINOLINE;2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-MethylBroMide
• CAS NO: 154057-56-4
• Molecular Formula: C₁₉H₁₅BrFN
• Molecular Weight: 356.23
• EINECS: 1308068-626-2
• Product Categories: intermediate
• Mol File: 154057-56-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 467.62 °C at 760 mmHg
• Flash Point: 236.608 °C
• Appearance: /
• Density: 1.461 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
• PKA: 4.32±0.50(Predicted)
• CAS DataBase Reference: 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline(154057-56-4)
• EPA Substance Registry System: 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline(154057-56-4)

Safety Data

• Hazardous Substances Data: 154057-56-4(Hazardous Substances Data)

Usage

Uses

3-(Bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline is used to prepare artificial HMG-CoA reductase inhibitors. It is also used to synthesize pitavastatin calcium via stereoselective Wittig olefination reaction.

Upstream product

• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 1356998-79-2 2-cyclopropyl-4-(4-fluorophenyl)-3-methylquinoline 
• 6704-19-4 1-cyclopropylpropan-1-one 
• 121660-11-5 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline 

Downstream Products

• 154057-57-5 diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate 
• 154057-58-6 <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 121660-11-5 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline 
• 586966-54-3 (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester 
• 147511-70-4 (R)-1-phenylethanamine (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoate 
• 146578-99-6 <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide 

Relevant articles and documents

Design, synthesis, α-amylase inhibition and in silico docking study of novel quinoline bearing proline derivatives

α-amylase enzyme hydrolyses carbohydrate into glucose is known to be an important molecular target for type 2 Diabetes mellitus. In the course of developing α-amylase enzyme inhibitors, we designed, synthesized seventeen novel quinoline bearing proline analogs, subsequently physico-chemical properties of designed analogs were also in silico predicted for their drug likeness evaluation. Synthesized compounds were characterized by spectral analysis such as Mass, IR, 1H NMR, 13C NMR and further screened in vitro for α-amylase inhibitory activity using acarbose as standard drug. Seven analogs, 6a, 6b, 6c, 6d, 6g, 10b and 10c showed significant α-amylase inhibitory activity. Eight analogs, 5, 6e, 6f, 6h, 6j, 10a, 10d and 10e showed good to moderate activity while other two analogs, 6i and 9 showed least activity. The molecular docking study of significantly active and weakly active compounds was performed in order to study their putative binding mode of the most and least active compounds (6c and 6i).

Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin

A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.

Synthesis, characterization of 3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline and its crystal structure

3-(Bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline (I), an important intermediate to synthesize pitavastatin calcium. It was prepared from ethyl 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxylate via reduction by KBH4/ZnCl2 and then bromide by PBr3. The product was characterized by NMR and LC-MS. The crystal structure of compound I was investigated using X-ray diffraction and SHELXTL-97 software. The result indicated that compound I crystallized in the triclinic system, space group P-1 with a = 9.6150(19), b = 9.868 (2), c = 10.060(2) ?, V = 783.3 (4) ?3; Z 2.