Methyl Acrylate → 3-{4-[3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-acrylic acid methyl ester

HRID 1617520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617520
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[Cl-].[NH4+].[C:28]([O:32][CH3:33])(=[O:31])[CH:29]=[CH2:30]>CN(C=O)C.C(N(CC)CC)C.CCOC(C)=O>[CH3:33][O:32][C:28](=[O:31])[CH:29]=[CH:30][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 7294Methyl AcrylateHCID 25517Ammonium ChlorideHCID 666681803-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Produkt 1

HCID 670155103-{4-[3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-acrylic acid methyl esterAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one ((example 74, step 5), 300 mg) in DMF (3 mL) tetrakis(triphenylphosphine)palladium (130 mg), methyl acrylate (0.103 mL) and triethylamine (0.16 mL) were added. The reaction mixture was stirred at 100° C. overnight, was cooled to room temperature and diluted with EtOAc and a saturated solution of ammonium chloride. The phases were separated and the inorganic one extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to yield the title compound (62 mg, 20%) as a yellow oil, MS (ESI+): m/z=400.1912 ([M+H]+).

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. customThe phases were separated
  3. extractionthe inorganic one extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6a579b1d5c7a4e94aff8dd763ff4a69a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765730B2

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