Z-6-chloro-3-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → 4'-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504589Notes

Reaction equation

HRID 504589 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]([C:34]([O:36][CH2:37][CH3:38])=[O:35])([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])/[C:9]1=[O:39])=O)(C)(C)C.[F:40][C:41]1[CH:42]=[CH:43][C:44]([CH3:56])=[C:45]([CH:47]=[N:48][C:49]([O:51][Si](C)(C)C)=[CH2:50])[CH:46]=1>C1(C)C=CC=CC=1>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][C:27]([C:34]([O:36][CH2:37][CH3:38])=[O:35])([CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH3:33])=[C:19]([CH:18]2[CH2:51][C:49](=[O:50])[NH:48][CH:47]([C:45]3[CH:46]=[C:41]([F:40])[CH:42]=[CH:43][C:44]=3[CH3:56])[C:10]32[C:11]2[C:16](=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:8][C:9]3=[O:39])[CH:24]=1

Participants

4

Reactant 2

HCID 67143622Z-6-chloro-3-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-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

Product 1

HCID 671438524'-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 9.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in Example 10d, E/Z-6-chloro-3-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-benzylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (1.3 g, 2.3 mmol) was reacted with 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (10 mmol) prepared in Example 1d in toluene to give the title compound as a white solid (150 mg).

Sources & evidence

ORD record
ord-7452a912d63549c4bcb984b58b272da6
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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