2-Methoxyethanol → 5-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid

Participants

Reaction Steps

NaH (2.26 g, 66 mmol) was added in portions to a solution of 2-methoxyethanol (30 mL). The mixture was stirred for 30 min at room temperature. Then 5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (Example 9 c, 3 g, 12 mmol) was added and the reaction mixture was heated to 100° C. overnight. The mixture was poured into water and extracted with ethyl acetate (30 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed three times with brine, dried (sodium sulfate) and evaporated. The crude title compound (2.48 g, yellow solid) was used for the next reaction step without further purification; MS (EI): m/e 276.0 [M+H]+.

Provenance & Evidence