Sodium Carbonate → 4-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine

HRID 1842517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842517
C(=O)([O-])[O-].[Na+].[Na+].[O:7]1[CH2:12][CH:11]=[C:10](B2OC(C)(C)C(C)(C)O2)[CH2:9][CH2:8]1.Br[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([F:29])[CH:24]=1.[Cl-].[NH4+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[O:7]1[CH2:12][CH:11]=[C:10]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([F:29])[CH:24]=2)[CH2:9][CH2:8]1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 27628514-Bromo-2-fluoropyridineHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Produkt 1

HCID 585484534-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of tetrakis(triphenylphosphine)palladium(0) (0.20 g, 0.17 mmol), aqueous sodium carbonate (2N aqueous, 8.52 mL, 17.05 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.43 g, 6.82 mmol), and 4-bromo-2-fluoropyridine (1.0 g, 5.68 mmol) in 1,2-dimethoxyethane (25 mL) was placed under argon atmosphere using 3 evacuation/backfill cycles. The mixture was then heated to 80° C. for 16 h then cooled to RT. Ethyl acetate and saturated aqueous ammonium chloride were added and the layers of the resulting biphasic mixture were separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 4-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine (0.90 g, 5.0 mmol, 89% yield) as a light yellow solid.

Aufarbeitung

  1. temperaturethen cooled to RT
  2. customthe layers of the resulting biphasic mixture were separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil that
  7. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-790dc212df1144088b1cb610fa84feae
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946230B2

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