Toluene → 6-chloro-4'-[5-chloro-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl phenyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504440
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([CH:15]=[N:16][C:17]([O:19][Si](C)(C)C)=[CH2:18])[CH:14]=1.C(OC([N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([Cl:41])[CH:39]=2)[C:34](=[CH:42][C:43]2[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:44]=2[O:50][C:51]([C:54]([O:56][CH2:57][CH3:58])=[O:55])([CH3:53])[CH3:52])[C:33]1=[O:59])=O)(C)(C)C>CO>[Cl:41][C:38]1[CH:39]=[C:40]2[NH:32][C:33](=[O:59])[C:34]3([CH:42]([C:43]4[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:44]=4[O:50][C:51]([C:54]([O:56][CH2:57][CH3:58])=[O:55])([CH3:53])[CH3:52])[CH2:19][C:17](=[O:18])[NH:16][CH:15]3[C:13]3[CH:14]=[C:9]([F:8])[CH:10]=[CH:11][C:12]=3[CH3:24])[C:35]2=[CH:36][CH:37]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 671438546-Chloro-3-[5-chloro-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterHCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

Produkt 1

HCID 765678816-chloro-4'-[5-chloro-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl phenyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a toluene solution (50 mL) of 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (77 mmol) was added E/Z 6-chloro-3-[5-chloro-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (8 g, 15.44 mmol). Then the reaction mixture were heated at 130° C. for 2. After the solution was cooled to room temperature, methanol was added, and then the mixture was concentrated. Then a mixture of trifluoroacetic acid (10 mL) and dichloromethane (30 mL) was added. The reaction mixture was stirred at room temperature for 10 min. The solution was concentrated and the residue was purified by Prep-HPLC to give title compound as a white solid (2.7 g).

Aufarbeitung

  1. temperatureAfter the solution was cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. additionThen a mixture of trifluoroacetic acid (10 mL) and dichloromethane (30 mL)
  4. additionwas added
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by Prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-65cb4171de0240f78ff3d896b4ad5edb
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776875B2

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