Sulfoxonium, trimethyl-, iodide (1:1) → Methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate

HRID 1512774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512774
[I-].C[S+](C)(C)=O.[CH3:7][Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:17][C:18]1[CH:19]=[C:20]([C:28]2[O:32][N:31]=[C:30]([C:33]3[CH:34]=[CH:35][CH:36]=[C:37]4[C:41]=3[N:40]([CH3:42])[CH:39]=[C:38]4/[CH:43]=[CH:44]\[C:45]([O:47][CH3:48])=[O:46])[N:29]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH:25]([CH3:27])[CH3:26]>CS(C)=O>[CH3:48][O:47][C:45]([CH:44]1[CH2:7][CH:43]1[C:38]1[C:37]2[C:41](=[C:33]([C:30]3[N:29]=[C:28]([C:20]4[CH:21]=[CH:22][C:23]([O:24][CH:25]([CH3:26])[CH3:27])=[C:18]([Cl:17])[CH:19]=4)[O:32][N:31]=3)[CH:34]=[CH:35][CH:36]=2)[N:40]([CH3:42])[CH:39]=1)=[O:46]

Komponenten

5

Edukt 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2724254Sodium bis(trimethylsilyl)amideHCID 59146121HCID 59146121, Verbindung

Produkt 1

HCID 67094311Methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a suspension of trimethylsulfoxonium iodide (234 mg) in DMSO (3 mL) stirred under nitrogen at 20° C. was added NaHMDS (1.0 mol/L in THF, 1.0 mL) dropwise during 5 mins. The reaction mixture was stirred at this temperature for 15 mins. A solution of methyl (2Z)-3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]-2-propenoate (D63) (120 mg) in DMSO was added dropwise. After addition was complete, the reaction was stirred at room temperature for 1.5 h, and then warmed to 50° C. for 4 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water, aqueous HCl (2 M) and brine, dried over sodium sulphate and evaporated to afford methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate (D65) (100 mg). MS (ES): C25H24ClN3O4 requires 465. found 466.2 (M+H+).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at this temperature for 15 mins
  2. additionAfter addition
  3. stirringthe reaction was stirred at room temperature for 1.5 h
  4. temperaturewarmed to 50° C. for 4 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. custompartitioned between ethyl acetate (25 mL) and water (25 mL)
  7. washThe organic phase was washed with water, aqueous HCl (2 M) and brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0634d4b9eef5475fb9f161071756848f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217028B2

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