Acetic Acid → 2,3-dihydro-1H-[2,3']bipyridinyl-4-one

HRID 1691833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691833
C[Si](C)(C)CCS([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=O)=O.[F-].[Cs+].C(O)(=O)C>CN(C=O)C.C(OCC)(=O)C>[NH:8]1[CH:13]=[CH:12][C:11](=[O:14])[CH2:10][CH:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 25953Cesium fluorideHCID 593777611-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3']bipyridinyl-4-one

Produkt 1

HCID 593777842,3-dihydro-1H-[2,3']bipyridinyl-4-oneAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1-(2-trimethylsilyl-ethanesulfonyl)-2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (106.1 mg, 0.31 mmol) in DMF (0.5 mL) was added cesium fluoride (153.5 mg, 1.0 mmol) under Ar atmosphere. The mixture was heated at 90° C. for 2 hours, then cooled to room temperature. Acetic acid (0.062 mL, 1.085 mmol) was added, and the mixture was diluted with ethyl acetate and filtered. The filtrate was taken to dryness under reduced pressure. Purification of the residue by flash chromatography (dichloromethane/methanol 95:5) gave 2,3-dihydro-1H-[2,3′]bipyridinyl-4-one (51 mg, 93.5%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customPurification of the residue by flash chromatography (dichloromethane/methanol 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-3ddaee935dfd46e299da634954db6b4a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153809B2

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