2-Pyridinamine, 5-iodo- → 2-(4'-Ethoxyphenyl)-6-iodoimidazo[1,2-a]pyridine

Temperature

110 °C

1.20 g (corresponding to 4.94 mmol) of 2-bromo-4′-ethoxyacetophenone and 1.09 g (corresponding to 4.95 mmol) of 2-amino-5-iodopyridine were dissolved in 20 mL of acetonitrile. The resulting solution was heated under reflux in an oil bath at 110° C. for 1.5 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered. Then, the precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 5 mL of methanol. Then, about 20 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 10 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 1.64 g (corresponding to 4.50 mmol) of 2-(4′-ethoxyphenyl)-6-iodoimidazo[1,2-a]pyridine (FIG. 3, Step 2).

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. washThen, the precipitates were washed with acetonitrile
7. customdried under reduced pressure
8. additionThen, about 20 mL of a saturated sodium hydrogencarbonate solution was added
9. customthe mixture was sonicated for 10 minutes
10. customPrecipitates
11. filtrationwere filtered
12. customrecovered from the resulting mixture
13. washsufficiently washed with water
14. customdried under reduced pressure

ORD record

ord-2901ee208675436f81f019d93eff8667

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207189B2