1-(2,3-Difluoro-6-isopropoxy-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 6-Chloro-4'-(3-chlorophenyl)-2'-(2,3-difluoro-6-isopropoxy-phenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728021Notes

Reaction equation

HRID 1728021 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)/[C:7](=[O:19])[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si](C)(C)C)=[CH:4][CH:3]=1.[F:28][C:29]1[C:34]([F:35])=[CH:33][CH:32]=[C:31]([O:36][CH:37]([CH3:39])[CH3:38])[C:30]=1[CH:40]=[N:41][C:42]([O:44][Si:45]([CH3:48])([CH3:47])[CH3:46])=[CH2:43]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:19])[C:6]3([CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[CH2:43][C:42](=[O:44])[NH:41][CH:40]3[C:30]3[C:31]([O:36][CH:37]([CH3:38])[CH3:39])=[CH:32][CH:33]=[C:34]([F:35])[C:29]=3[F:28])[C:5]2=[CH:4][CH:3]=1.[CH3:11][O:12][CH:13]([Si:45]([CH3:46])([CH3:47])[CH3:48])[CH3:14]

Participants

4

Reactant 2

HCID 702623811-(2,3-Difluoro-6-isopropoxy-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615089Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one

Product 1

HCID 775806616-Chloro-4'-(3-chlorophenyl)-2'-(2,3-difluoro-6-isopropoxy-phenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 55b, E/Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one prepared in example 55a (3.4 g, 8.10 mmol) was reacted with 1-(2,3-difluoro-6-isopropoxy-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (16 g, 51.1 mmol) prepared in example 62c in toluene to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(2,3-difluoro-6-isopropoxy-phenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as an off-white solid.

Sources & evidence

ORD record
ord-c732ab92417d435fbf39e3f7de5a0eca
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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