| Identification | Back Directory | [Name]
3-benzyl-6-bromo-2-methoxyquinoline | [CAS]
654655-69-3 | [Synonyms]
Bedaquiline Impurity A
Bedaquiline Impurity 12
3-benzyl-6-bromo-2-methoxyquinoline
6-Bromo-2-methoxy-3-benzylquinoline
3-BENZYL 1-6-BROMO-2-METHOXYQUINOLINE
6-bromo-2-methoxy-3-(phenylmethyl)-Quinoline
Quinoline, 6-bromo-2-methoxy-3-(phenylmethyl)-
Bedaquiline int-2 3-Benzyl-6-bromo-2-methoxyquinoline | [EINECS(EC#)]
207-791-3 | [Molecular Formula]
C17H14BrNO | [MDL Number]
MFCD22493488 | [MOL File]
654655-69-3.mol | [Molecular Weight]
328 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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