654655-69-3

White Solid

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

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.

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