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Methanol → 6-Chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1174054
Notes
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Reaction equation

HRID 1174054 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH:8]=[N:9][C:10]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH2:11])[CH:7]=1.[Cl:18][C:19]1[CH:27]=[C:26]2[C:22](/[C:23](=[CH:37]/[C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=3)/[C:24](=[O:36])[N:25]2[CH2:28][O:29][CH2:30][CH2:31][Si](C)(C)C)=[CH:21][CH:20]=1.CO>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:27]=[C:26]2[NH:25][C:24](=[O:36])[C:23]3([CH:37]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=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:22]2=[CH:21][CH:20]=1.[CH3:28][O:29][CH:30]([Si:13]([CH3:14])([CH3:15])[CH3:16])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 701785041-(5-Fluoro-2-methylphenyl)-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 775807686-Chloro-4'-(3-chlorophenyl)-2'-(5-fluoro-2-methylphenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneYield 49%

Reagents, catalysts & solvents

1
HCID 1140TolueneSolvent

Procedure

To a solution of 1-(5-fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 1c in toluene (50 mL) was added E/Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one prepared in example 1b (3.0 g, 7.14 mmol). The reaction mixture was stirred under nitrogen in a sealed tube at 1480G for 40 min. After the solution was cooled to room temperature, methanol (50 mL) was added, and then the mixture was concentrated. The residue was purified by chromatography (EtOAc:Hexane=2:1) to give racemic (2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-2,3-dihydro-2,6′-dioxo spiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as an off-white solid (Yield 2.1 g, 49%).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by chromatography (EtOAc:Hexane=2:1)

Sources & evidence

ORD record
ord-2f3ab56064d448a5a1ea9822680deee4
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834179B2

Reaction notes

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