Cesium fluoride → methyl 2(S)-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate

HRID 1864555

Reaktionsgleichung

Reaktionsgleichung von HRID 1864555
Br[C:2]1[N:7]=[C:6]([N:8]([CH3:19])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[CH:5]=[CH:4][CH:3]=1.[CH2:20]([O:22][C@@H:23]([CH2:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])[CH3:21].[F-].[Cs+]>COC(O)C(O)OC>[CH2:20]([O:22][C@@H:23]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([N:8]([CH3:19])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10])[N:7]=2)=[CH:31][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])[CH3:21]

Komponenten

5

Edukt 3

HCID 25953Cesium fluorideHCID 67147872methyl 2(S)-ethoxy-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]propanoateHCID 860188681-(6-Bromopyrid-2-yl)-1-methyl-3-heptylurea

Produkt 1

HCID 67148298methyl 2(S)-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoateAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21263609Dimethoxy ethylene glycolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3.2 g (9.7 mmol) of 1-(6-bromopyrid-2-yl)-3-heptyl-1-methylurea, 4.2 g (12.6 mmol) of methyl 2(S)-ethoxy-3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]propanoate (prepared as in Example 7e) and 4.4 g (29.1 mmol) of caesium fluoride are placed in 200 ml of dimethoxyethylene glycol. The reaction medium is degassed, 0.23 g (0.3 mmol) of dichlorodiphenylphosphinoferrocenepalladium is then added and the reaction medium is stirred at 80° C. for 18 hours. After addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is washed with water, with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with an 80/20 heptane/ethyl acetate mixture. 2 g (45%) of methyl 2(S)-ethoxy-3-{4-[6-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate are obtained.

Aufarbeitung

  1. customThe reaction medium is degassed
  2. addition0.23 g (0.3 mmol) of dichlorodiphenylphosphinoferrocenepalladium is then added
  3. additionAfter addition of water
  4. extractionthe reaction medium is extracted with ethyl acetate
  5. washThe organic phase is washed with water, with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue obtained
  10. customis purified by thin-layer chromatography on silica
  11. washeluted with an 80/20 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-565c6c6f751240c8bd3bf1cb2f73e607
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625914B2

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