Реакция #2146686

ord-4bc09b23fe4a40ff938a0b354a991ac2

Уравнение реакции

O=C(CBr)c1ccc(O)cc1
2-bromo-4′-hydroxyacetophenone
COc1ccc(N)nc1
2-amino-5-methoxypyridine
COc1ccc2nc(-c3ccc(O)cc3)cn2c1
2-(4′-hydroxyphenyl)-6-methoxyimidazo[1,2-a]pyridine
Выход 81.6%

Реагенты

Нет

Растворители

Условия реакции

Температура
90°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеAfter the completion of the reaction
  2. 2
    Температураthe reaction solution was cooled down to room temperature
  3. 3
    Другоеprecipitates
  4. 4
    Фильтрацияwere filtered
  5. 5
    Другоеrecovered
  6. 6
    ПромывкаThe precipitates were washed with acetonitrile
  7. 7
    Другоеdried under reduced pressure
  8. 8
    workup.ADDITIONThen, about 20 mL of a saturated sodium hydrogencarbonate solution was added
  9. 9
    Другоеthe mixture was sonicated for 5 minutes
  10. 10
    ДругоеPrecipitates
  11. 11
    Фильтрацияwere filtered
  12. 12
    Другоеrecovered from the resulting mixture
  13. 13
    Промывкаsufficiently washed with water
  14. 14
    Другоеdried under reduced pressure

Методика

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 precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 40 mL of water and 40 mL of methanol. Then, about 20 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 5 minutes using a ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently 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. 2, Step 5).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08277777B2uspto-grants-2012_10