Water → 4-(2-Fluoropyridin-3-YL)tetrahydro-2H-pyran-4-carbaldehyde

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Reaktionsgleichung

[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[O:8])[CH2:3][CH2:2]1.Br[C:10]1[C:11]([F:16])=[N:12][CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O.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>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:16][C:11]1[C:10]([C:4]2([CH:7]=[O:8])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:15][CH:14]=[CH:13][N:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Into a sealed tube was added tetrahydro-2H-pyran-4-carbaldehyde (0.25 g, 2.190 mmol), 3-bromo-2-fluoropyridine (0.321 g, 1.825 mmol), palladium(ii) acetate (0.016 g, 0.073 mmol), cesium carbonate (0.714 g, 2.190 mmol), water (1.644 μL, 0.091 mmol), BINAP (0.068 g, 0.110 mmol) in Dioxane (7.30 mL). The resulting mixture was heated to 100° C. overnight. More catalyst and ligand (palladium(ii) acetate (0.016 g, 0.073 mmol), binap (0.068 g, 0.110 mmol)) were added and the resulting mixture was heated to 113° C. until the starting material was completely consumed. Aqueous work up followed by DCM extraction. Purification by Biotage (0-100% MeOH/DCM) & prep-plate TLC (5% MeOH/DCM) produced product which was advanced to the next step.

Aufarbeitung

temperaturethe resulting mixture was heated to 113° C. until the starting material
customwas completely consumed
extractionAqueous work up followed by DCM extraction
customPurification by Biotage (0-100% MeOH/DCM)
customproduced product which

Quellen und Nachweise

ORD-Eintrag: ord-53f38231f3934b48adf1fea40065f156
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08759532B2

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