Cesium carbonate → Tert-butyl 4-(6-fluoropyridin-3-yl)piperazine-1-carboxylate

HRID 271560

Reaktionsgleichung

Reaktionsgleichung von HRID 271560
Cl.[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].Br[C:16]1[CH:17]=[CH:18][C:19]([F:22])=[N:20][CH:21]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.CCCCCC.O>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[N:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Komponenten

10

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2755973Tert-butyl Piperazine-1-carboxylate HydrochlorideHCID 27831685-Bromo-2-fluoropyridine

Produkt 1

HCID 59834735Tert-butyl 4-(6-fluoropyridin-3-yl)piperazine-1-carboxylateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of piperazine-1-carboxylic acid tert-butyl ester hydrochloride (0.75 mmol), 5-bromo-2-fluoropyridine (0.90 mmol), (R)-2,2′-bis(diphenylphosphino)-1, 1′-binaphthyl (0.038 mmol), palladium acetate (0.038 mmol) and cesium carbonate (1.8 mmol) in toluene is stirred at 80° C. for 7 h and then 100° C. for 4 h, and poured into water. The mixture is extracted with AcOEt. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. The crude product is purified by silica gel column chromatography to give the product in 43% yield. Rf=0.61 (n-hexane:AcOEt=1:1)

Aufarbeitung

  1. wait100° C. for 4 h
  2. extractionThe mixture is extracted with AcOEt
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography
  7. customto give the product in 43% yield

Quellen und Nachweise

ORD-Eintrag
ord-61ffb66676194eb78c51d58eeeef3fb6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452886B2

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