4-Bromopyridine → tert-Butyl 4-(pyridin-4-yl)piperazine-1-carboxylate

HRID 46001

Reaktionsgleichung

Reaktionsgleichung von HRID 46001
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[N:8]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2].O>[N:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:10][CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][CH2:12]2)=[CH:3][CH:4]=1

Komponenten

10

Edukt 4

HCID 142684-BromopyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 57436818tert-Butyl 4-(pyridin-4-yl)piperazine-1-carboxylateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a degassed solution of 4-bromopyridine (1 equiv.), tert-butyl piperazine-1-carboxylate (16 mmol, 1.2 equiv.) and NaOtBu (3.4 equiv.) in toluene were added Pd(OAc)2 (2 mol %) and BINAP (1 mol %) and the resulting solution was refluxed for 3 h. The reaction mixture was cooled, diluted with ethyl acetate and given water and brine washes respectively. The organic layer was dried over sodium sulfate, the solvent removed in vacuo and the crude product purified by column chromatography (silica). Yield: 47%.

Aufarbeitung

  1. temperaturethe resulting solution was refluxed for 3 h
  2. temperatureThe reaction mixture was cooled
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent removed in vacuo
  5. customthe crude product purified by column chromatography (silica)

Quellen und Nachweise

ORD-Eintrag
ord-1fb23cebb0544832ac7e9595990b2180
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541573B2

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