2-Amino-5-methoxypyridine → HCID 68719554, compound

Temperature

110 °C

1.46 g (corresponding to 4.28 mmol) of 2-bromo-4′-hydroxy-3′-iodoacetophenone and 584 mg (corresponding to 4.71 mmol) of 2-amino-5-methoxypyridine were dissolved in 30 mL of acetonitrile. The resulting solution was heated under reflux in an oil bath at 110° C. for 2.5 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 3.0 mL of water and 1.0 mL of methanol. Then, about 10 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 5 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure, to obtain 812 mg (corresponding to 2.22 mmol) of 2-(4′-hydroxy-3′-iodophenyl)-6-methoxyimidazo[1,2-a]pyridine (FIG. 5, Step 1).

1. temperatureThe resulting solution was heated
2. customAfter the completion of the reaction
3. temperaturethe reaction solution was cooled down to room temperature
4. customprecipitates
5. filtrationwere filtered
6. customrecovered
7. washThe precipitates were washed with acetonitrile
8. customdried under reduced pressure
9. additionThen, about 10 mL of a saturated sodium hydrogencarbonate solution was added
10. customthe mixture was sonicated for 5 minutes
11. customPrecipitates
12. filtrationwere filtered
13. customrecovered from the resulting mixture
14. washsufficiently washed with water
15. customdried under reduced pressure

ORD record

ord-91fa93df278d45f5a89ceed061d1e730

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399672B2