Nitrogen → (S)-tert-Butyl 4-(4,5-dimethyl-6-phenylpyridazin-3-yl)-2-methylpiperazine-1-carboxylate

HRID 2093359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093359
N#N.Cl[C:4]1[N:9]=[N:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:12]([CH3:23])[CH2:11]2)=[C:6]([CH3:24])[C:5]=1[CH3:25].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[F-].[Cs+]>O1CCOCC1>[CH3:24][C:6]1[C:5]([CH3:25])=[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:9]=[N:8][C:7]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:12]([CH3:23])[CH2:11]1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 58359254(S)-tert-butyl 4-(6-chloro-4,5-dimethylpyridazin-3-yl)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 58359248(S)-tert-Butyl 4-(4,5-dimethyl-6-phenylpyridazin-3-yl)-2-methylpiperazine-1-carboxylateAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Treat a N2 degassed mixture of (S)-tert-butyl 4-(6-chloro-4,5-dimethylpyridazin-3-yl)-2-methylpiperazine-1-carboxylate (3.03 g, 8.87 mmol), phenylboronic acid (1.62 g, 13.3 mmol), and CsF (4.09 g, 26.9 mmol) in 1,4-dioxane (120 mL) with (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) chloride (1.08 g, 1.32 mmol). Heat the reaction mixture at 95° C. overnight. Cool the reaction, and partition between EtOAc and H2O. Wash the organic layer with brine, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 15 to 85% EtOAc in hexanes) to afford the title compound as a white solid (2.93 g, 86%). ES/MS m/z 383.0 (M+1).

Aufarbeitung

  1. customdegassed
  2. temperatureCool
  3. customthe reaction
  4. custompartition between EtOAc and H2O
  5. washWash the organic layer with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customPurify the residue by flash silica gel chromatography (gradient of 15 to 85% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-02ab26925b524505a6e29cd6bc0292a9
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445493B2

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