3,4-Diethoxybenzamide → 2-(3,4-Diethoxyphenyl)-4-(pyridin-4-yl)oxazole

HRID 447905

Reaktionsgleichung

Reaktionsgleichung von HRID 447905
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[C:18]([NH2:20])=[O:19])[CH3:13].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:12]([O:14][C:15]1[CH:16]=[C:17]([C:18]2[O:19][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=3)[N:20]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[CH3:13]

Komponenten

5

Edukt 3

HCID 3403423,4-DiethoxybenzamideHCID 516892Sodium BicarbonateHCID 27762394-(Bromoacetyl)pyridine hydrobromide

Produkt 1

HCID 591454902-(3,4-Diethoxyphenyl)-4-(pyridin-4-yl)oxazoleAusbeute 2,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

In a microwave vial were dissolved 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (134 mg, 0.478 mmol) and 3,4-diethoxybenzamide (100 mg, 0.478 mmol) in DMF (5 ml) and the reaction was heated at 170° C. for 40 min. The reaction mixture was poured in a saturated solution of NaHCO3 and extracted with EtOAc (50 ml×3). The combined organic phases were washed with a saturated solution of NaCl (2×30 ml) and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (95:5) to yield 4 mg (2.7%) of the product. MS (EI) m/z: 311 (M+).

Aufarbeitung

  1. extractionextracted with EtOAc (50 ml×3)
  2. washThe combined organic phases were washed with a saturated solution of NaCl (2×30 ml)
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1cbbe5f4707249608310bc9af3103b6b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481573B2

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