1,1-Dichloroacetone → 2-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole

HRID 1392234

Reaktionsgleichung

Reaktionsgleichung von HRID 1392234
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([NH2:15])=[O:14])=[CH:7]2.[Cl:18][CH:19](Cl)[C:20](=O)[CH3:21]>C1(C)C=CC=CC=1.CN(C=O)C>[Cl:18][CH2:19][C:20]1[N:15]=[C:13]([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:12][CH:11]=3)[O:14][CH:21]=1

Komponenten

4

Edukt 2

HCID 105671,1-DichloroacetoneHCID 692204685-trifluoromethoxy-1H-indole-2-carboxylic acid amide

Produkt 1

HCID 1363319652-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21735183Dimethylformamide tolueneLösungsmittel

Versuchsvorschrift

5-trifluoromethoxy-1H-indole-2-carboxylic acid amide (4.5 g, 18.43 mmol) and dichloro acetone (3.5 g, 27.63 mmol) in toluene/DMF (5:1, 30 ml) were kept at reflux temperature for 24 h with continuous removal of water by applying a Dean-Stark trap (a water separator used in chemical reactions). After removal of solvents in vacuo, the residue was intensively shaken with water, the precipitate was isolated by filtration and washed with water and brine. After evaporation of the solvents in vacuo chromatography on silica gel (iso-hexanes/ethyl acetate 3:1) yielded 2-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole as off white solid. Yield 2.6 g (44%)

Aufarbeitung

  1. temperatureat reflux temperature for 24 h
  2. customwith continuous removal of water
  3. customAfter removal of solvents in vacuo
  4. customthe precipitate was isolated by filtration
  5. washwashed with water and brine
  6. customAfter evaporation of the solvents in vacuo chromatography on silica gel (iso-hexanes/ethyl acetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-35d9fe1c0382458985c64c3771cf6172
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342030B2

Verknüpfte Notizen

Wird geladen…