(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate → Tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

HRID 1616061

Reaktionsgleichung

Reaktionsgleichung von HRID 1616061
O=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=O>CC(O)C.O.O.[Na+].Cl[Au-](Cl)(Cl)Cl>[F:27][C:24]1[CH:23]=[C:22]2[C:21](=[CH:26][CH:25]=1)[N:20]=[C:2]([CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])[C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[C:28]2[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1

Komponenten

5

Edukt 2

HCID 58318617(S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamateHCID 69673534(2-Amino-5-fluorophenyl)(pyridin-2-yl)methanone

Produkt 1

HCID 67595333Tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamateAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 18949434Sodium tetrachloroaurate dihydrateKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate (0.427 g, 1.615 mmol), (2-amino-5-fluorophenyl)(pyridin-2-yl)methanone (0.384 g, 1.777 mmol), and sodium tetrachloroaurate(III) dihydrate (0.032 g, 0.081 mmol) in 2-propanol (9.50 mL) was heated under reflux. After 71 h, the mixture was cooled to rt and evaporated to dryness. The mixture was dissolved in DCM (50 mL) and washed with brine (1×50 mL), and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.423 g, 0.952 mmol, 58.9% yield) as orange syrupy solid: LC-MS (ESI) m/z 445.1 [M+H]+. The orange syrupy solid was used without further purification. Epimerization occurred during the condensation.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customevaporated to dryness
  4. dissolutionThe mixture was dissolved in DCM (50 mL)
  5. washwashed with brine (1×50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude material
  10. customThe crude material was purified by silica gel column chromatography
  11. washeluting with a gradient of 0% to 50% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4e9f237989d0437ebe59229c1852881c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765768B2

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