1-(5-Chloro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 4'-[5-chloro-2-(1-ethyl-1-methoxycarbonyl-propoxy)-phenyl]-6-chloro-2'-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504567Notes

Reaction equation

HRID 504567 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)/[C:10](=[CH:18]/[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][C:27]([CH2:34][CH3:35])([C:30]([O:32][CH3:33])=[O:31])[CH2:28][CH3:29])/[C:9]1=[O:36])=O)(C)(C)C.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([CH3:53])=[C:42]([CH:44]=[N:45][C:46]([O:48][Si](C)(C)C)=[CH2:47])[CH:43]=1>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:36])[C:10]3([CH:18]([C:19]4[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=4[O:26][C:27]([CH2:28][CH3:29])([C:30]([O:32][CH3:33])=[O:31])[CH2:34][CH3:35])[CH2:47][C:46](=[O:48])[NH:45][CH:44]3[C:42]3[CH:43]=[C:38]([Cl:37])[CH:39]=[CH:40][C:41]=3[CH3:53])[C:11]2=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 702039431-(5-Chloro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86632089Z-3-[5-chloro-2-(1-ethyl-1-methoxycarbonyl-propoxy)-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 722961904'-[5-chloro-2-(1-ethyl-1-methoxycarbonyl-propoxy)-phenyl]-6-chloro-2'-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 19.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in Example 10d, E/Z-3-[5-chloro-2-(1-methoxycarbonyl-1-ethyl-propoxy)-benzylidene]-6-chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.63 g, 4.9 mmol) prepared in Example 62f was reacted with 1-(5-chloro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (20 mmol) prepared in Example 13b in toluene (20 mL) to give the title compound as a white solid (600 mg).

Sources & evidence

ORD record
ord-dbdd4cd2285d4c3b8846cd86de472606
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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