Cesium carbonate → HCID 57800261, Verbindung

HRID 913654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913654
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2)[CH2:2][CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:26][C:27]1[N:31]=[C:30]([C:32]2[C:33]([S:38][CH3:39])=[N:34][CH:35]=[CH:36][CH:37]=2)[O:29][N:28]=1>C(#N)C>[CH3:39][S:38][C:33]1[C:32]([C:30]2[O:29][N:28]=[C:27]([CH2:26][N:5]3[C:6]4[C:11](=[C:10]([C:13]([F:15])([F:16])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=4)[CH:12]=[C:4]3[CH2:1][CH2:2][CH3:3])[N:31]=2)=[CH:37][CH:36]=[CH:35][N:34]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27967603-[3-(Chloromethyl)-1,2,4-oxadiazol-5-yl]-2-(methylsulfanyl)pyridineHCID 674051552-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Produkt 1

HCID 57800261HCID 57800261, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 153A) (0.100 g, 0.396 mmol) in anhydrous acetonitrile (20 mL) was added Cs2CO3 (1.30 g, 4.00 mmol) and 3-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]-2-(methylthio)pyridine (0.170 g, 0.594 mmol). The mixture was heated under N2, for 2 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-20% EtOAc-hexanes gradient) to afford a pure product (0.152 g, 84% yield): MS (ES) m/z 458 (M+).

Aufarbeitung

  1. temperatureThe mixture was heated under N2, for 2 h
  2. temperatureUpon cooling
  3. customthe mixture was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-20% EtOAc-hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5197df2afb3141389301911028866d4e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026262B2

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