Iodine → 5-[1,3]Dioxolan-2-yl-2-fluoro-3-iodo-pyridine

HRID 561012

Reaktionsgleichung

Reaktionsgleichung von HRID 561012
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([F:12])=[N:10][CH:11]=1.C([N-]C(C)C)(C)C.[Li+].[I:21]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([I:21])[C:9]([F:12])=[N:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 2724682Lithium diisopropylamideHCID 601557925-(1,3-Dioxolan-2-YL)-2-fluoropyridine

Produkt 1

HCID 669977985-[1,3]Dioxolan-2-yl-2-fluoro-3-iodo-pyridineAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cool a solution of 5-[1,3]dioxolan-2-yl-2-fluoro-pyridine (2.0 g, 11.8 mmol) in THF (20 mL) to −75° C. Add lithium diisopropylamide (2 M in THF, 6 mL, 12 mmol) over a period of 30 min. Stir the mixture for an additional 3 hours. Add iodine (3.0 g, 11.8 mmol, dissolved in 100 mL of THF). Stir for 2 hours after the addition is complete. Add water (100 mL) to the mixture and allow the temperature to rise to room temperature over 1 hour while stirring. Treat the mixture with saturated aqueous sodium thiosulfate solution (50 mL). Extract the solution with ether. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (hexane to 20% ethyl acetate in hexane) to afford the title compound (2.1 g, 60%) as a yellow oil. MS (ES) m/z 296 [M+1]+.

Aufarbeitung

  1. stirringStir for 2 hours
  2. additionafter the addition
  3. waitto rise to room temperature over 1 hour
  4. stirringwhile stirring
  5. extractionExtract the solution with ether
  6. concentrationConcentrate the solution in vacuo to a brown oil
  7. customPurify by column chromatography (hexane to 20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-237c637b693a4df39d152726d1b7412e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063212B2

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