Cesium carbonate → 5-[2-(1,3-Dioxolan-2-yl)ethoxy]-2-fluoropyridine

HRID 81627

Reaktionsgleichung

Reaktionsgleichung von HRID 81627
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C(=O)C.[F:21][C:22]1[N:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C(OCC)(=O)C.O>[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][O:28][C:25]1[CH:24]=[CH:23][C:22]([F:21])=[N:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 27631086-Fluoropyridin-3-ol

Produkt 1

HCID 684307205-[2-(1,3-Dioxolan-2-yl)ethoxy]-2-fluoropyridineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-(2-Bromoethyl)-1,3-dioxolane (2.49 ml, 19.9 mmol) and cesium carbonate (15.1 g, 46.4 mmol) were added to an N,N-dimethylacetamide solution (25 ml) of 6-fluoropyridin-3-ol (1.5 g, 13.3 mmol), and stirred under a nitrogen atmosphere at 100° C. for 12 hours. The reaction solution was cooled with ice, water and ethyl acetate were added, and the organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=5:1 to 1:1) to obtain 5-[2-(1,3-dioxolan-2-yl)ethoxy]-2-fluoropyridine (2.43 g, yield: 86%) as a colorless oil.

Aufarbeitung

  1. additionwere added
  2. washthe organic layer was washed with water and saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=5:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2479298fb2b74637adf8974f0fe5c0c8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846700B2

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