3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline

Bezeichnung:3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline

CAS-Nr154057-56-4

Englisch Name:3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline

CBNumberCB02470335

SummenformelC19H15BrFN

Molgewicht356.23

MOL-Datei154057-56-4.mol

3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline physikalisch-chemischer Eigenschaften

Schmelzpunkt	131-134°C
Siedepunkt	467.6±45.0 °C(Predicted)
Dichte	1.461±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
pka	4.32±0.50(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
InChI	InChI=1S/C19H15BrFN/c20-11-16-18(12-7-9-14(21)10-8-12)15-3-1-2-4-17(15)22-19(16)13-5-6-13/h1-4,7-10,13H,5-6,11H2
InChIKey	QCNHMJKMLPPGMF-UHFFFAOYSA-N
SMILES	N1C2C(=CC=CC=2)C(C2=CC=C(F)C=C2)=C(CBr)C=1C1CC1

Gefahreninformationscode (GHS)

3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
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.
Synthese

1356998-79-2

154057-56-4

Example 17: Preparation of 3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)quinoline (PTVBR) PTVME (0.85 g, 3.06 mmol) and N-bromosuccinimide (NBS, 1.16 g, 2.1 eq.) were dissolved in a solvent mixture of acetonitrile (MeCN, 20 mL) and carbon tetrachloride (CCl4, 5 mL). The reaction mixture was irradiated for 4 days at room temperature (~20 °C) using light at a wavelength of 254 nm. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residual oil was redissolved in dichloromethane (CH2Cl2, 20 mL). The organic phase was washed sequentially with saturated sodium thiosulfate solution (Na2S2O3, 1 × 10 mL), saturated sodium bicarbonate solution (NaHCO3, 2 × 10 mL), and brine (1 × 10 mL) and dried with anhydrous magnesium sulfate (MgSO4). After removing the solvent under reduced pressure, the product was purified by column chromatography (elution gradient: 1-10% ethyl acetate/n-heptane solution) to give PTVBR (0.22 g, 20% yield). 1H NMR (CDCl3): δ 1.17 (2H, m), 1.40 (2H, m), 2.50-2.54 (1H, m), 4.6 (2H, s), 7.24-7.40 (6H, m), 7.64 (1H, m), 8.00-8.02 (1H, m) ppm. 13C NMR (CDCl3): δ 9.8, 14.7, 29.1, 115.6, 115.8, 125.8, 126.2, 126.4, 127.4, 128.5, 128.8, 129.7, 130.87, 130.91, 131.0, 131.60, 131.63, 146.9, 147.1. 161.4, 161.5, 163.9 ppm.
Einzelnachweise
[1] Patent: WO2012/13325, 2012, A1. Location in patent: Page/Page column 65-66
[2] Patent: EP2423195, 2012, A1. Location in patent: Page/Page column 57-58

3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline Upstream-Materialien And Downstream Produkte

3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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