1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → Racemic (2'S,3S,4'R)-6-chloro-4'-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504491
[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][CH2:44][C:45]2([CH3:49])[CH2:48][O:47][CH2:46]2)/[C:26]1=[O:50])=O)(C)(C)C>C1(C)C=CC=CC=1>[Cl:34][C:31]1[CH:32]=[C:33]2[NH:25][C:26](=[O:50])[C:27]3([CH:35]([C:36]4[CH:41]=[C:40]([Cl:42])[CH:39]=[CH:38][C:37]=4[O:43][CH2:44][C:45]4([CH3:49])[CH2:48][O:47][CH2:46]4)[CH2:12][C:10](=[O:11])[NH:9][CH:8]3[C:6]3[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:17])[C:28]2=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86632063Z-6-Chloro-3-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 74928827Racemic (2'S,3S,4'R)-6-chloro-4'-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 1,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (7.1 mmol) in anhydrous toluene (7 mL) was added E/Z-6-Chloro-3-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.7 g, 1.4 mmol). The solution was stirred under Ar in a sealed tube at 140° C. for 3 h. After the solution was cooled to room temperature and concentrated, the residue was purified by chromatography (DCM:CH3OH=50:1) to give crude product. The crude product was purified again by Prep-HPLC to give title compound as a white solid (12 mg).

Aufarbeitung

  1. temperatureAfter the solution was cooled to room temperature
  2. concentrationconcentrated
  3. customthe residue was purified by chromatography (DCM:CH3OH=50:1)
  4. customto give crude product
  5. customThe crude product was purified again by Prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-28369a2802484b23914a754ac17f7ffe
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776875B2

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