3-benzyl-6-bromo-2-methoxyquinoline Chemical Properties

Melting point:

82-83℃

Boiling point:

420.5±40.0 °C(Predicted)

Density 

1.388±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

2.45±0.50(Predicted)

color 

Off-White

InChI

InChI=1S/C17H14BrNO/c1-20-17-14(9-12-5-3-2-4-6-12)10-13-11-15(18)7-8-16(13)19-17/h2-8,10-11H,9H2,1H3

InChIKey

WMFHVNYOCKTDMX-UHFFFAOYSA-N

SMILES

N1C2C(=CC(Br)=CC=2)C=C(CC2=CC=CC=C2)C=1OC

3-benzyl-6-bromo-2-methoxyquinoline Usage And Synthesis

Chemical Properties

White Solid

Uses

3-benzyl-6-bromo-2-methoxyquinoline is a reactant used in the preparation of Bedaquiline (B119550), a potential drug in the treatment of tuberculosis.

Synthesis

3-Benzyl-6-bromo-2-chloroquinoline (20 g, 0.06 mol) was dissolved in anhydrous methanol (100 mL), followed by the addition of a methanolic solution of 15% sodium methanolate (108 g). The reaction mixture was refluxed overnight with stirring. Upon completion of the reaction, the mixture was cooled to room temperature and stored at -20 °C overnight to induce precipitation of the product. The crude product 3-benzyl-6-bromo-2-methoxyquinoline precipitated as white needle-like crystals. The solid product was separated by filtration, washed with water and dried in air to give 19 g (96% yield) of the target compound as a white solid.

References

[1] ChemMedChem, 2017, vol. 12, # 2, p. 106 - 119
[2] Tetrahedron, 2007, vol. 63, # 2, p. 451 - 460
[3] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 790 - 792
[4] Patent: WO2005/70430, 2005, A1. Location in patent: Page/Page column 34-35
[5] Patent: WO2006/67048, 2006, A1. Location in patent: Page/Page column 27

3-benzyl-6-bromo-2-methoxyquinoline(654655-69-3)Related Product Information

• Ethyl isonicotinate
• Bedaquiline fumarate
• Bedaquiline Impurity 4
• Quinoline, 2-methoxy-3-(phenylmethyl)-
• Benzenepropanamide, N-(2-bromophenyl)-
• Peroxyacetic acid
• Formic acid
• 3-(DIMETHYLAMINO)-1-(NAPHTHALEN-1-YL)PROPAN-1-ONE HYDROCHLORIDE
• (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE
• CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester
• 4-Bromo-2-nitroaniline
• 4-Pyrimidinamine, 2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-
• 5-BROMO-2-(2-METHYL-2H-TETRAZOL-5-YL)-PYRIDINE
• 2,5-Dichloro-N-[2-[(1-methylethyl)thio]phenyl]-4-pyrimidinamine
• 3-benzyl-6-bromo-2-chloroquinoline
• 3-(dimethylamino)-1-(naphthalen-5-yl)propan-1-one
• 2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine
• 5-Methyl-2-(1-Methylethoxy)-4- (4-piperidinyl)- BenzenaMine hydrochloride (1:2)