Lactic Acid → N-[5-Bromo-2-(methyloxy)-3-pyridinyl]-2-hydroxypropanamide

Participants

Reaction Steps

2-Hydroxypropanoic acid (444 mg, 4.93 mmol) was dissolved in DCM (10 ml) and (1-chloro-2-methyl-1-propen-1-yl)dimethylamine (0.652 ml, 4.93 mmol) was added. The mixture was stirred for 5 mins, then 5-bromo-2-(methyloxy)-3-pyridinamine (500 mg, 2.463 mmol, available from Asymchem) was added and the reaction mixture was diluted with further DCM (5 ml). Stirring was continued at room temperature, then after 3 hours a further portion of chloro-2-methyl-1-propen-1-yl)dimethylamine (0.652 mL, 4.93 mmol) was added and the reaction was left stirring at room temperature overnight. The mixture was quenched with water and the separated DCM layer was washed with saturated sodium bicarbonate (aq) before passing through a hydrophobic frit and evaporation to dryness. The residue was stirred with 2M NaOH (aq., 5 ml). After stirring for 4 hours the resulting precipitate was collected by filtration and then dissolved in DCM and washed with 2M HCl (aq). The DCM layer was separated. The remaining aqueous layer was washed with ethyl acetate and the combined organics were evaporated to dryness to afford the title compound (220 mg).

Provenance & Evidence