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

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

Used in Pharmaceutical Industry:
3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline is used as a key intermediate in the synthesis of artificial HMG-CoA reductase inhibitors. These inhibitors play a crucial role in lowering cholesterol levels and are essential for the treatment of various cardiovascular diseases.
Additionally, 3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline is utilized in the synthesis of pitavastatin calcium, a widely prescribed drug for hyperlipidemia, through a stereoselective Wittig olefination reaction. This reaction allows for the creation of specific stereoisomers, which are vital for the drug's efficacy and safety.

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

• 146578-99-6 <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyl(diphenyl)phosphine oxide 
• 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 

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).

Preparation method of pitavastatin calcium intermediate

The invention relates to a preparation method of a pitavastatin calcium intermediate, which comprises the following steps: (1) under the protection of nitrogen, carrying out chemical reaction on compounds N7 and NBS and a solvent at 30-80 DEG C to prepare

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.

Pitavastatin calcium method for the preparation of

The invention relates to a preparation method of a cholesterol reduction drug, particularly relates to a preparation method of pitavastatin calcium as a crude drug of the cholesterol reduction drug, and aims at the problems that the pitavastatin calcium synthetic technology in the prior art is long in steps and complicated in operation, and uses strongly corrosive reagents which is environmentally unfriendly, causes serious corrosion to equipment, and may not facilitate industrial production. The invention provides the new preparation method of the pitavastatin calcium, the new preparation method is as follows: 3-bromomethyl-2-cyclopropyl-4-(4-fluorophenyl)quinoline is prepared from 2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde by a one step reaction, and then reacts with an organophosphorus reagent to obtain pitavastatin calcium intermediate phosphorus ylide, on the basis of improving of the yield to 80%, the reaction steps are reduced, and the reaction difficulty is reduced, and hydroxylamine hydrochloride is selected as a deprotection reagent, so that the new preparation method is mild in reaction conditions, environmentally friendly, high in yield, and beneficial to industrial production.

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.

METHOD FOR PREPARATION OF PITAVASTATIN AND ITS PHARMACEUTICAL ACCEPTABLE SALTS THEREOF

The present invention discloses a compound, which is alkali or alkaline earth metal salts of pitavastatin, wherein the alkali or earth metal comprise one or more of magnesium, zinc, potassium, strontium and barium.

PITAVASTATIN CALCIUM AND PROCESS FOR ITS PREPARATION

The invention provides the process for the preparation of pitavastatin and its pharmaceutically acceptable salts thereof. In particular, the invention provides a process for the preparation of stable pitavastatin calcium in crystalline form having water content less than 5% wt/wt. The present invention also provides stable crystalline form of pitavastatin calcium substantially free from crystal Form-A and use thereof for pharmaceutical compositions.

NOVEL POLYMORPHS OF PITAVASTATIN CALCIUM

The present invention provides a solid of pitavastatin tert-butyl ester and process for its preparation. The present invention also provides a novel crystalline form of pitavastatin calcium, process for its preparation and pharmaceutical compositions comprising it.

PROCESS FOR THE PREPARATION OF KEY INTERMEDIATES FOR THE SYNTHESIS OF STATINS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof

The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.