Reaction #2146699

Reaction equation

2-bromo-4′-hydroxyacetophenone

2-amino-5-iodopyridine

→

2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

Yield 78.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherAfter the completion of the reaction
2. 2
   Temperaturethe reaction solution was cooled down to room temperature
3. 3
   Otherprecipitates
4. 4
   Filtrationwere filtered
5. 5
   Otherrecovered
6. 6
   WashThe precipitates were washed with acetonitrile
7. 7
   Otherdried under reduced pressure
8. 8
   Otherwas sonicated for 5 minutes with an ultrasonic washing machine
9. 9
   OtherPrecipitates
10. 10
    Filtrationwere filtered
11. 11
    Otherrecovered from the resulting mixture
12. 12
    Washwashed with water
13. 13
    Otherdried under reduced pressure

Procedure

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. The suspension was supplemented with about 10 mL of a saturated sodium hydrogencarbonate solution, and was sonicated for 5 minutes with an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, 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. 6, Step 2).

Source