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Water → ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate

HRID 1475866
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1475866
O.C(=O)([O-])[O-].[K+].[K+].[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[C:18]1[CH:23]=[CH:22][N:21]([CH2:24][CH2:25][C:26]([CH3:36])([S:32]([CH3:35])(=[O:34])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:20](=[O:37])[C:19]=1[CH3:38]>O1CCOCC1.[Pd]>[CH3:36][C:26]([S:32]([CH3:35])(=[O:34])=[O:33])([CH2:25][CH2:24][N:21]1[CH:22]=[CH:23][C:18]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:19]([CH3:38])[C:20]1=[O:37])[C:27]([O:29][CH2:30][CH3:31])=[O:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 67249750ethyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Produkt 1

HCID 67248376ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Water (1 mL) was added to a suspension of potassium carbonate (392 mg, 2.84 mg), phenylboronic acid (76.1 mg, 0.624 mmol), and ethyl 4-(4-iodo-3-methyl-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate (250 mg, 0.567 mmol) in 1,4-dioxane (5 mL) at ambient temperature. To this mixture was added Pd EnCat™ (154 mg, 0.06 mmol) and the mixture was stirred at 80° C. overnight. The mixture was cooled to ambient temperature, filtered, diluted with ethyl acetate and washed with water. To the organic extract was added silica gel and the mixture was concentrated to dryness. The material was purified via silica gel chromatography eluting with ethyl acetate/heptanes to afford ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate as an oil. 118.3 mg

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. extractionTo the organic extract
  6. additionwas added silica gel
  7. concentrationthe mixture was concentrated to dryness
  8. customThe material was purified via silica gel chromatography
  9. washeluting with ethyl acetate/heptanes

Quellen und Nachweise

ORD-Eintrag
ord-78c64e13bcae43e9af94f813b4081999
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018384B2

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