Sodium hydride → 2-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenoxymethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole

HRID 1392236

Reaktionsgleichung

Reaktionsgleichung von HRID 1392236
[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=[N:4]1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[NH:27][C:28]3[C:33]([CH:34]=2)=[CH:32][C:31]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:30][CH:29]=3)[O:24][CH:25]=1>CN(C)C=O>[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:20][C:21]3[N:22]=[C:23]([C:26]4[NH:27][C:28]5[C:33]([CH:34]=4)=[CH:32][C:31]([O:35][C:36]([F:39])([F:37])[F:38])=[CH:30][CH:29]=5)[O:24][CH:25]=3)=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=[N:4]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 1363319652-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole

Produkt 1

HCID 1355203662-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenoxymethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (7 mg, 0.28 mmol) was given at 0° C. to a solution of 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol (55 mg, 0.25 mmol) in 2.0 ml N,N-dimethyl formamide and stirred for 30 min. 2-(4-Chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole (80 mg, 0.25 mmol) dissolved in 1.0 ml N,N-dimethyl formamide was added at 0° C. and stirring continued at 0° C. for 1 h and 12 h at room temperature thereafter. The mixture was quenched with water (10 ml) and extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (10 ml), dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel (ethyl acetate) yielded 2-{4-[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenoxymethyl]-oxazol-2-yl}-5-trifluoromethoxy-1H-indole as off white solid. Yield 50 mg (40%)

Aufarbeitung

  1. additionwas added at 0° C.
  2. stirringstirring
  3. waitcontinued at 0° C. for 1 h and 12 h at room temperature
  4. customThe mixture was quenched with water (10 ml)
  5. extractionextracted with ethyl acetate (3×10 ml)
  6. washThe combined organic extracts were washed with brine (10 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d96f986343c47f9bfdc59cf06a51a99
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342030B2

Verknüpfte Notizen

Wird geladen…