Water → 6-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

HRID 1620408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620408
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7](/[CH:13]=C/N(C)C)[N:6]=1.O.I([O-])(=O)(=O)=[O:25].[Na+]>C1COCC1>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH:13]=[O:25])[N:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 23667635Sodium periodateHCID 86664562(E)-6-(2,4-Difluorophenoxy)-2-(2-(dimethylamino)vinyl)nicotinonitrile

Produkt 1

HCID 848198116-(2,4-Difluorophenoxy)-2-formylnicotinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At RT, to the product of step 2 above in THF (70.00 mL) and water (70.00 mL) was added sodium periodate (8.9 g, 42 mmol) in one portion and the reaction mixture was allowed to stir at RT for 2 h, resulting in the formation of a yellow suspension. The suspension was passed through a flitted funnel, washing with THF (2×10 mL). The filtrate was concentrated under reduced pressure and the remaining mixture was extracted with DCM (2×30 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. Purification on the ISCO (40 g column, 20-60% EtOAc in hexanes) afforded 6-(2,4-difluorophenoxy)-2-formylnicotinonitrile as a light yellow crystalline solid. MS (ESI, pos.ion) m/z: M+1=261.0

Aufarbeitung

  1. customresulting in the formation of a yellow suspension
  2. customThe suspension was passed through a flitted funnel
  3. washwashing with THF (2×10 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionthe remaining mixture was extracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on the ISCO (40 g column, 20-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-89bca07b03de484bbddf0e28ee5344bf
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772481B2

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