Water → 4-(6-Methoxyimidazo[1,2-a]pyridin-2-yl)phenol

Temperature

90 °C

2.15 g (corresponding to 10.0 mmol) of 2-bromo-4′-hydroxyacetophenone and 1.25 g (corresponding to 10.0 mmol) of 2-amino-5-methoxypyridine were dissolved in 50 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 90° C. for 3.5 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The recovered precipitates were washed with acetonitrile, and dried under reduced pressure to obtain crude crystals. The resulting crude crystals were suspended in a mixed solution of 40 mL of water and 40 mL of methanol. The suspension was supplemented with about 20 mL of a saturated sodium hydrogencarbonate solution, and sonicated for 5 minutes by an ultrasonic washing machine. The precipitates were filtered and recovered from the resulting mixture, washed with water, and dried under reduced pressure, to obtain 1.96 g (corresponding to 8.16 mmol) of 2-(4′-hydroxyphenyl)-6-methoxyimidazo[1,2-a]pyridine (FIG. 1, Step 5).

1. customAfter the completion of the reaction
2. temperaturethe reaction solution was cooled down to room temperature
3. customprecipitates
4. filtrationwere filtered
5. customrecovered
6. customThe recovered precipitates
7. washwere washed with acetonitrile
8. customdried under reduced pressure
9. customto obtain crude crystals
10. customsonicated for 5 minutes by an ultrasonic washing machine
11. filtrationThe precipitates were filtered
12. customrecovered from the resulting mixture
13. washwashed with water
14. customdried under reduced pressure

ORD record

ord-7c830b610b5d45eeabb47d068e7deef6

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08277777B2