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

HRID 1728079Notes

Reaction equation

HRID 1728079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[N:9][C:10]([O:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH2:11])[CH:5]=[CH:6][CH:7]=1.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21](/[C:22](=[CH:36]/[C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=3[CH3:44])/[C:23](=[O:35])[N:24]2[CH2:27][O:28][CH2:29][CH2:30][Si](C)(C)C)=[CH:20][CH:19]=1.CO>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:26]=[C:25]2[NH:24][C:23](=[O:35])[C:22]3([CH:36]([C:37]4[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=4[CH3:44])[CH2:12][C:10](=[O:11])[NH:9][CH:8]3[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:21]2=[CH:20][CH:19]=1.[CH3:27][O:28][CH:29]([Si:13]([CH3:14])([CH3:15])[CH3:16])[CH3:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 68961886HCID 68961886, compoundHCID 86615100Z-6-chloro-3-(5-fluoro-2-methyl-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one

Product 1

HCID 775809006-Chloro-2'-(3-chlorophenyl)-4'-(5-fluoro-2-methyl-phenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a toluene (12 ml) solution of 1-(3-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 1b in toluene (50 mL) was added E/Z-6-chloro-3-(5-fluoro-2-methyl-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one (0.30 g, 0.72 mmol) prepared in example 146a. The reaction tube was then placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated for 35 min at 135° C. After the solution was cooled to room temperature, methanol (25 mL) was added. The reaction solutions were concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:3) to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-(5-fluoro-2-methyl-phenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a yellow solid (0.45 g)

Workup

  1. customThe reaction tube was then placed into the cavity of a focused monomode microwave reactor
  2. customthe contents of the flask were irradiated for 35 min at 135° C
  3. concentrationThe reaction solutions were concentrated
  4. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:3)

Sources & evidence

ORD record
ord-0f4e49f503224557b4107a615dcad3e4
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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