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Nitrogen → 2-(4-Bromo-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

HRID 1189390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1189390
N#N.C([O-])([O-])=O.[K+].[K+].[CH2:9]([O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:19]OS(C)(=O)=O)[O:17][CH:18]=1)=[O:13])[CH3:10].[Br:25][C:26]1[CH:27]=[N:28][NH:29][CH:30]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CC(C)=O>[CH2:9]([O:11][C:12]([C:14]1[N:15]=[C:16]([CH2:19][N:28]2[CH:27]=[C:26]([Br:25])[CH:30]=[N:29]2)[O:17][CH:18]=1)=[O:13])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 866649112-Methanesulfonyloxymethyl-oxazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 671284292-(4-Bromo-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236
Tetrabutylammonium Bromide
Katalysator
HCID 180AcetoneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), K2CO3 (356 mg, 2.55 mmol) was added at rt to a solution of 2-methanesulfonyloxymethyl-oxazole-4-carboxylic acid ethyl ester (127 mg, 0.51 mmol), TBAB (33 mg, 0.10 mmol) and 4-bromo-1H-pyrazole (76 mg, 0.51 mmol) in acetone (5.0 mL). After stirring at rt for 2 h, the solvent was removed under reduced pressure. The residue was partitioned between water and EA, the two layers were separated and the aq. layer was extracted twice with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as an orange solid. TLC: rf (1:1 hept-EA)=0.27. LC-MS-conditions 01: tR=0.84 min, [M+H]+=299.96.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between water and EA
  3. customthe two layers were separated
  4. extractionthe aq. layer was extracted twice with EA
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b73c348886d34503abe221913ef0de69
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08674111B2

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