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Potassium Phosphate, Tribasic → Tert-butyl 4-(3-cyclopropyl-2-fluorobenzoyl)piperazine-1-carboxylate

HRID 1172455
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1172455
Br[C:2]1[C:3]([F:23])=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:6].[CH:24]1(B(O)O)[CH2:26][CH2:25]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:24]1([C:2]2[C:3]([F:23])=[C:4]([CH:20]=[CH:21][CH:22]=2)[C:5]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[O:6])[CH2:26][CH2:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 57562603Tert-butyl 4-(3-bromo-2-fluorobenzoyl)piperazine-1-carboxylate

Produkt 1

HCID 57562614Tert-butyl 4-(3-cyclopropyl-2-fluorobenzoyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 107 mg of tert-butyl 4-(3-bromo-2-fluorobenzoyl)piperazine-1-carboxylate in 2.0 ml of toluene and 0.1 ml of water was added 72 mg of cyclopropylboronic acid, 3.2 mg of palladium acetate, 0.052 ml of tricyclohexylphosphine (15% toluene solution) and 207 mg of potassium phosphate, successively. The reaction solution was stirred at 150° C. for 10 minutes using a microwave reaction apparatus. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then concentrated. The residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=1/1) to give the title compound.

Aufarbeitung

  1. customa microwave reaction apparatus
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-3af61690d81549679bb88b34690dcf3c
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834018B2

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