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Potassium Fluoride → 3-Formyl-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine

HRID 1377474
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1377474
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].[F-].[K+].[CH3:16][O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Br)=[O:19]>C(#N)C.[OH-].[Na+]>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:23][C:22]3[C:25]([CH3:29])=[CH:26][CH:27]=[CH:28][C:21]=3[NH:20][C:18]([O:17][CH3:16])=[O:19])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2]
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Komponenten

6

Edukt 3

HCID 522689Potassium FluorideHCID 22914806HCID 22914806, VerbindungHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Produkt 1

HCID 229148053-Formyl-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridineAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798
Sodium Hydroxide
Katalysator
HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

2.6 g of 3-formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine are dissolved in 50 ml of dry acetonitrile with exclusion of moisture at 50° C. and, after cooling to RT, 2.8 g of commercial potassium fluoride (50% by weight) on kieselguhr (for example Celite®) are added. A solution of 3.6 g of 2-methoxycarbonylamino-6-methylbenzyl bromide in 50 ml of dry acetonitrile is added dropwise, and the mixture is heated at 70° C. for 6 h. After cooling to RT, the mixture is poured into ice-water, adjusted to pH 9 with a few drops of 6N sodium hydroxide solution and extracted with ethyl acetate. The collected organic phases are washed with water and dried over sodium sulfate. Stripping off the solvent in vacuo and stirring in a little cold methanol result in 3.2 g of the title compound of m.p. 196°-198° C.

Aufarbeitung

  1. temperaturethe mixture is heated at 70° C. for 6 h
  2. temperatureAfter cooling to RT
  3. extractionextracted with ethyl acetate
  4. washThe collected organic phases are washed with water
  5. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-ec75cfac7f3c418489cf5a794ba7da4c
Quelldatensatz
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05665730

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