2-Bromo-1-(4-hydroxyphenyl)ethanone → 2-(4'-Hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

Temperature

110 °C

441 mg (corresponding to 2.0 mmol) of 2-bromo-4′-hydroxyacetophenone and 449 mg (corresponding to 2.0 mmol) of 2-amino-5-iodopyridine were dissolved in 15 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110° C. for 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 10 mL of water and 10 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 526 mg (corresponding to 1.56 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine (FIG. 1-10, Step 2). The NMR measurement results of the resulting 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine (internal standard: dimethylsulfoxide) are shown below.

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. washThe precipitates were washed with acetonitrile
7. customdried under reduced pressure
8. additionThen, about 10 mL of a saturated sodium hydrogencarbonate solution was added
9. customthe mixture was sonicated for 5 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-c5fcc84947d3420a840b235faf3be7d2

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08303935B2