Methyl iodide → HCID 59146081, Verbindung

HRID 1512843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512843
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([F:33])=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[K+].[CH3:36]I.[NH4+].[Cl-]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[C:18]([F:33])=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:36])[CH:23]=[C:22]4[CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 59146158Ethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-6-fluoro-1H-indol-3-yl]propanoate

Produkt 1

HCID 59146081HCID 59146081, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To the solution of ethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-6-fluoro-1H-indol-3-yl]propanoate (D146) (320 mg) in dimethyl sulfoxide (5 mL) was added KOH (152 mg) and MeI (0.64 mL). The reaction solution was stirred at room temperature overnight. Saturated aqueous NH4Cl (10 mL) solution was added, and the resulting solution was extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with brine and dried over sodium sulphate. The organic solution was concentrated to afford ethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-6-fluoro-1-methyl-1H-indol-3-yl]propanoate (D147) (330 mg). MS (ES): C25H25ClFN3O4 requires 485; found 486.2 (M+H+).

Aufarbeitung

  1. extractionthe resulting solution was extracted with ethyl acetate (3×10 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationThe organic solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4b45b2c5ac0d4eb1b52152eaca99a9ca
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217028B2

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