Potassium Carbonate → 1'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one

HRID 2036118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036118
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.[NH:14]1[CH2:18][CH2:17][C:16]2([C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:27])[CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:14]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][C:19]4=[O:27])[CH2:15]3)=[CH:7][CH:6]=2)[O:12][N:11]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 10954296Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-oneHCID 167322943-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine

Produkt 1

HCID 685546001'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine (690 mg) obtained in Example 43(2), spiro[indole-3,3′-pyrrolidin]-2(1H)-one (800 mg), potassium carbonate (500 mg) and tetrabutylammonium iodide (130 mg) were suspended in N,N-dimethylformamide-tetrahydrofuran (1:1, v/v, 50 mL), and the suspension was stirred at 120° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with aqueous sodium carbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. Ethyl acetate was added and the resulting precipitate was collected by filtration, and recrystallized from ethyl acetate to give the object product (750 mg, 62%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with aqueous sodium carbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionEthyl acetate was added
  6. filtrationthe resulting precipitate was collected by filtration
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8b967e958ac5430e88063481c8156955
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575167B2

Notizen zur Reaktion

Wird geladen…