Water → 2-(4-Methoxyphenyl)imidazo[1,2-a]pyridine

HRID 66015

Reaktionsgleichung

Reaktionsgleichung von HRID 66015
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=O.O>C(O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:6]=[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]3[CH:14]=2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 104392-AminopyridineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 6949632-(4-Methoxyphenyl)imidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 25.2 g. of sodium bicarbonate, 12.3 g. of 2-aminopyridine and 30 g. of α-bromo-p-methoxyacetophenone in 100 ml. of water and 550 ml. of absolute ethanol is heated at reflux temperatures for 1.5 hrs. The reaction mixture is concentrated under reduced pressure to a yellow solid, which is partitioned between chloroform and water. The organic layer is separated, dried over sodium sulfate. Removal of the chloroform in vacuo leaves the crude intermediate as a yellow solid. Recrystallization from ethanolwater give 15.2 g. of the desired material, m.p. 131-134° C.

Aufarbeitung

  1. additionA mixture of 25.2 g
  2. temperatureat reflux temperatures for 1.5 hrs
  3. concentrationThe reaction mixture is concentrated under reduced pressure to a yellow solid, which
  4. customis partitioned between chloroform and water
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the chloroform in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09cb52c6912f41c58ce343688b1c7262
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04129567

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