Cesium fluoride → Ethyl 3-{2-(3-methoxypropoxy)-3'-[methyl(morpholin-4-ylcarbonyl)amino]biphenyl-4-yl}propanoate

HRID 1690636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690636
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:10]=[CH:11][C:12]=1OS(C(F)(F)F)(=O)=O.[CH3:28][N:29]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40](B2OC(C)(C)C(C)(C)O2)[CH:39]=1)[C:30]([N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[O:31].[F-].[Cs+]>COCCOC.C(O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:10]=[CH:11][C:12]=1[C:42]1[CH:41]=[CH:40][CH:39]=[C:38]([N:29]([CH3:28])[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])[CH:43]=1

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 66906419N-methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine-4-carboxamideHCID 86633298Ethyl 3-[3-(3-methoxypropoxy)-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate

Produkt 1

HCID 66906220Ethyl 3-{2-(3-methoxypropoxy)-3'-[methyl(morpholin-4-ylcarbonyl)amino]biphenyl-4-yl}propanoateAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Ethyl 3-[3-(3-methoxypropoxy)-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl]propanoate (1.0 g, 2.40 mmol) was, dissolved in 1,2-dimethoxyethane (14.4 ml) and ethanol (1.6 ml). N-methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine-4-carboxamide (0.914 g, 2.64 mmol) was added and argon was bubbled in the solution for 10 minutes. Cesium fluoride (0.80 g, 5.28 mmol) and palladium tetrakistriphenylphosphine (0.139 g, 0.12 mmol) were added and the mixture was heated to reflux under an argon atmosphere for 14 hours. After cooling to room temperature, solvents were evaporated under reduced pressure and the residue was dissolved in ethyl acetate and water. The organic phase was washed with saturated aqueous ammonium chloride and brine, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 7/3) giving 0.232 g (20%) of the desired product.

Aufarbeitung

  1. customargon was bubbled in the solution for 10 minutes
  2. temperaturethe mixture was heated
  3. temperatureto reflux under an argon atmosphere for 14 hours
  4. customsolvents were evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe organic phase was washed with saturated aqueous ammonium chloride and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-c5c19f0978674289b4639c743fec2ac8
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153647B2

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