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

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]+.

1. temperaturethe reaction mixture was heated to 100° C. overnight
2. extractionextracted with ethyl acetate (30 mL)
3. additionThe pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid
4. extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
5. washThe combined organic extracts were washed three times with brine
6. dry with materialdried (sodium sulfate)
7. customevaporated
8. customThe crude title compound (2.48 g, yellow solid) was used for the next reaction step without further purification

ORD record

ord-e0eeb0c690e747088721d58adaaf3ea1

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321727B2