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Water → Ethyl 5-cyclopropyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate

HRID 219564
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 219564
C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C:17]([CH:19]1[CH2:21][CH2:20]1)=O)[CH3:13].[N:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])=[N+:24]=[N-:25].O>CN(C=O)C>[CH:19]1([C:17]2[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:24]=[N:25][C:16]=2[C:15]([O:14][CH2:12][CH3:13])=[O:22])[CH2:21][CH2:20]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 116079241-Azido-2-fluorobenzene

Produkt 1

HCID 68649104Ethyl 5-cyclopropyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

DBU (2.99 ml; 20.06 mmol; 1.10 eq.) was dissolved in DMF (37.5 ml) and put under nitrogen atmosphere. 3-Cyclopropyl-3-oxo-propionic acid ethyl ester (Betapharma, 3.132 g; 20.06 mmol; 1.10 eq.) was added to the mixture and it was stirred for 15 min. Then a solution of 1-azido-2-fluorobenzene prepared according to Platz, M. S. et al. J. Org. Chem. 1989, 54, 5938-5945, (2.5 g; 18.23 mmol; 1 eq.) in DMF (5 mL) was added dropwise to the solution at room temperature. Water (50 mL) was added to the cooled reaction mixture and the aqueous layer was extracted with EtOAc (3×50 mL). Combined organics were washed with water and brine, dried over MgSO4 and concentrated under vacuum affording the title compound as a brown oil. It was used in the next step without further purification. LC/MS (Method B): 276.1 (M+H)+.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  2. washCombined organics were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-59ffb5b717d145edbe0ffa8943f7b38d
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202856B2

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