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

HRID 1873372
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1873372
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][N:16]=1>C(#N)C>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][N:16]3[CH:2]=2)=[CH:6][CH:7]=1)[CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 885792-Pyridinamine, 5-iodo-HCID 21130602-Bromo-1-(4-ethoxyphenyl)ethanone

Produkt 1

HCID 247570152-(4'-Ethoxyphenyl)-6-iodoimidazo[1,2-a]pyridineAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

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 refluxed 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. 2-3, Step 2).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. temperaturethe reaction solution was cooled down to room temperature
  3. customprecipitates
  4. filtrationwere filtered
  5. washThen, the precipitates were washed with acetonitrile
  6. customdried under reduced pressure
  7. additionThen, about 20 mL of a saturated sodium hydrogencarbonate solution was added
  8. customthe mixture was sonicated for 10 minutes
  9. customPrecipitates
  10. filtrationwere filtered
  11. customrecovered from the resulting mixture
  12. washsufficiently washed with water
  13. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6b461483c43e47bb9cf89a9039b13f47
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08303935B2

Notizen zur Reaktion

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