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Dimethylformamide → tert-Butyl4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxylate

HRID 1044563
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1044563
[F-].[K+].IC1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[F:23][C:24]([Si](C)(C)C)([F:26])[F:25].C[N:32](C=O)C>CCOC(C)=O.[Cu]I>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][N:10]([C:6]2[CH:5]=[N:32][CH:9]=[C:8]([C:24]([F:26])([F:25])[F:23])[CH:7]=2)[CH2:15][CH2:14]1)=[O:17])([CH3:20])([CH3:21])[CH3:22]
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Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilane2×HCID 68596930Tert-butyl 4-(3-iodophenyl)piperazine-1-carboxylate

Produkt 1

HCID 59833555tert-Butyl4-[5-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Copper(I) iodide (0.49 g, 2.6 mmol) and potassium fluoride (0.15 g, 2.6 mmol) in a flask were flame-heated under gentle shaking and at high vacuum until a greenish color appeared. A solution of tert-butyl 4-(3-iodophenyl)piperazine-1-carboxylate (0.5 g, 1.0 mmol) and (trifluoromethyl)trimethylsilane (0.37 g, 2.6 mmol) in DMF (5 mL) was added. The brown solution was stirred at room temperature overnight. More (trifluoromethyl)trimethylsilane (0.37 g) was added. The mixture was heated at 50° C. overnight, diluted with EtOAc and washed with saturated ammonium chloride. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4), concentrated and purified by flash chromatography on silica gel (20% to 40% EtOAc/hexanes) to give 120 mg of desired product. MS calculated for C15H20F3N3O2: (M+H) 332; found 332.1.

Aufarbeitung

  1. stirringThe brown solution was stirred at room temperature overnight
  2. washwashed with saturated ammonium chloride
  3. extractionThe aqueous layer was extracted with EtOAc three times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (20% to 40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9e0bb04e25884271af48f1915293575d
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563582B2

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