Hydrochloric Acid → Methyl 2-(5-broMopyridin-2-yl)acetate

Temperature

100 °C

Concentrated hydrochloric acid (10 mL) was added to a solution of 5-(5-bromo-1H-2-pyridinylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (Example 44-(1); 4.53 g, 15.09 mmol) in dioxane (20 mL), and the mixture was stirred at 100° C. for one hour. After cooling, the reaction mixture was concentrated. The residue was dissolved in methanol (20 mL) and toluene (20 mL). Trimethylsilyldiazomethane (2 M solution in diethyl ether, 25 mL) was added, and the mixture was stirred at room temperature for 30 minutes. Acetic acid was added to the reaction mixture to terminate the reaction. Then, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70, 40 minutes) to give the target compound as a colorless oil (2.50 g, 72%).

1. temperatureAfter cooling
2. concentrationthe reaction mixture was concentrated
3. dissolutionThe residue was dissolved in methanol (20 mL)
4. additionTrimethylsilyldiazomethane (2 M solution in diethyl ether, 25 mL) was added
5. stirringthe mixture was stirred at room temperature for 30 minutes
6. additionAcetic acid was added to the reaction mixture
7. customto terminate
8. customthe reaction
9. concentrationThen, the mixture was concentrated under reduced pressure
10. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70, 40 minutes)

ORD record

ord-b67055e7aaac41ceb8b338daf9f9725d

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935688B2