1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 4'-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-5-chloro-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504467
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH:8]=[N:9][C:10]([O:12][Si](C)(C)C)=[CH2:11])[CH:7]=1.C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([Cl:34])[CH:32]=2)/[C:27](=[CH:35]/[C:36]2[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=2[O:43][CH:44]2[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]2)/[C:26]1=[O:57])=O)(C)(C)C>C1(C)C=CC=CC=1>[C:53]([O:52][C:50]([N:47]1[CH2:48][CH2:49][CH:44]([O:43][C:37]2[CH:38]=[CH:39][C:40]([Cl:42])=[CH:41][C:36]=2[CH:35]2[CH2:12][C:10](=[O:11])[NH:9][CH:8]([C:6]3[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:17])[C:27]32[C:28]2[C:33](=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[NH:25][C:26]3=[O:57])[CH2:45][CH2:46]1)=[O:51])([CH3:56])([CH3:54])[CH3:55]

Komponenten

4

Edukt 2

HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86632057Z-3-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-5-chloro-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 749285074'-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-5-chloro-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 24,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (15 mL, 30 mmol) in toluene (50 mL) was added E/Z-3-[2-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-5-chloro-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (3.6 g, 6 mmol). The reaction mixture was stirred under argon at 65° C. for 3 h and then heated at 130° C. for 4 h. After cooled to room temperature, the mixture was concentrated. The residue was purified by chromatography to give the title compound as a white solid (Yield: 1 g).

Aufarbeitung

  1. temperatureheated at 130° C. for 4 h
  2. temperatureAfter cooled to room temperature
  3. concentrationthe mixture was concentrated
  4. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bd1a0ffa811349e1a32917d1f770dfb0
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776875B2

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