Methyl iodide → 5-bromo-N-(5-chlorothiazol-2-yl)-1'-methylspiro[indoline-3,3'-pyrrolidine]-1-carboxamide

HRID 1411238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1411238
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.[C:24](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([CH3:24])[CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71522964HCID 71522964, Verbindung

Produkt 1

HCID 904497475-bromo-N-(5-chlorothiazol-2-yl)-1'-methylspiro[indoline-3,3'-pyrrolidine]-1-carboxamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The 5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (48.2 mg, 0.105 mmol) obtained in Example 2 was dissolved in N,N′-dimethylformamide (1.0 mL). Thereafter, potassium carbonate (43.5 mg, 0.315 mmol) and methyl iodide (30.0 mg, 0.210 mmol) were added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 3 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with methylene chloride. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (11.0 mg, 35%) in the form of a white solid.

Aufarbeitung

  1. extractionwas then extracted with methylene chloride
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-9f844f6c2ea6492bae8807416674da96
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921576B2

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