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

Melting point:

131-134°C

Boiling point:

467.6±45.0 °C(Predicted)

Density 

1.461±0.06 g/cm3(Predicted)

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)

form 

Solid

color 

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

3-(Bromomethyl)-2-cyclopropyl-4-(4'-fluorophenyl)quinoline Usage And Synthesis

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.

Synthesis

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.

References

[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(154057-56-4)Related Product Information

• Tert-buthyl Pitavastatin
• tert-Butyl (4R-cis)-6-formaldehydel-2,2-dimethyl-1,3-dioxane-4-acetate
• (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl-2-propenal
• (3S,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic Acid CalciuM Salt
• (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid
• (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic Acid CalciuM Salt
• (4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
• Benzenepropanoic acid,a-hydroxy-b-methoxy-b-phenyl-,methyl ester
• 2-HYDROXY-3-METHOXY-3,3-DIPHENYLPROPANOIC ACID
• BenzaMide, 2-benzoyl-
• 2-(4-Fluor-benzoyl)-benzamid
• PITAVASTATIN LACTONE
• 2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carboxaldehyde
• 2-Cyclopropyl-3-[(diphenylphosphinyl)methyl]-4-(4-fluorophenyl)quinoline
• (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile
• 2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-methanol
• Pitavastatin calcium
• [2-Cyclopropyl-4-(4-fluorophenyl)-quinolin-3-ylmethyl]-triphenyl-phosphonium bromido