Hydrochloric Acid → Methyl 3-bromo-2-pyridinecarboxylate

1.01 g of 3-bromo-2-cyanopyridine was added to methanol (18 mL) solution of 1.55 g of sodium methoxide, and in a nitrogen atmosphere, this was stirred at room temperature for 1.5 hours and then at 70° C. for 2.5 hours. The reaction liquid was cooled to room temperature, and 30 mL of 2 N hydrochloric acid was added thereto and stirred at room temperature for 4 hours. Then, aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline water, and dried with anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1) to obtain 135 mg of the entitled compound as a colorless oily substance.

1. waitat 70° C. for 2.5 hours
2. customThe reaction liquid
3. temperaturewas cooled to room temperature
4. stirringstirred at room temperature for 4 hours
5. extractionextracted with ethyl acetate
6. washThe ethyl acetate layer was washed with saturated saline water
7. dry with materialdried with anhydrous sodium sulfate
8. customthe solvent was evaporated off under reduced pressure
9. customThe residue was separated
10. custompurified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 4/1)

ORD record

ord-d3b840267c3f4dc6819f0a71d60fb206

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855294B2