Cesium fluoride → Tert-butyl 4-(6-phenylpyridin-2-yl)piperazine-1-carboxylate

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Reaktionsgleichung

Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[F-].[Cs+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]1([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[CH:5]=[CH:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 2 g (5.84 mmol) of tert.butyl 4-(6-bromo-pyridin-2-yl)-piperazine-1-carboxylate, 0.75 g (6.15 mmol) of phenylboric acid, 2.66 g (17.52 mmol) of caesium fluoride, 0.045 g (0.15 mmol) of 2-(di-t-butylphosphino)-biphenyl and 0.013 g (0.06 mmol) of palladium acetate in 20 ml of dioxane is stirred for six hours at 50° C. under nitrogen. Then it is diluted with water and the reaction mixture is extracted with ethyl acetate. The organic phase is separated off and dried over sodium sulphate. Purification is by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=4:1).

Aufarbeitung

extractionthe reaction mixture is extracted with ethyl acetate
customThe organic phase is separated off
dry with materialdried over sodium sulphate
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-3b84e28124a0406f8caf8f62a0e66e56
Quelldatensatz: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06818644B1

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