5-Chlorooxindole → HCID 69659086, compound

HRID 1829036Notes

Reaction equation

HRID 1829036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:22]([N:29]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[C:35](=O)[O:34][CH2:33]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(COC)OC.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:35]1[C:36]2[C:32](=[CH:31][C:30]([N:29]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:38][CH:37]=2)[CH2:33][O:34]1

Participants

6

Reactant 3

HCID 1528015-ChlorooxindoleHCID 2733832Lithium HexamethyldisilazideHCID 220614885-(Dibenzylamino)-2-benzofuran-1(3H)-one

Product 1

HCID 69659086HCID 69659086, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-chlorooxindole (63 mg, 0.371 mmol) in dimethoxyethane (2.0 ml) at room temperature was added 1.0M LiHMDS in THF (742 μl). After the mixture was stirred for 10 minutes at room temperature, 5-dibenzylamino-3H-isobenzofuran-1-one (110 mg, 0.334 mmol) was added, and the reaction was rapidly stirred at room temperature for 1.5 hours. The mixture was quenched into 4% HCl (20 ml), and then stirred with EtOAc. The mixture was basified with saturated NaHCO3 aqueous solution. The organic layer was diluted with MeOH, followed by addition of HCl in MeOH to give a yellow precipitant. The yellow precipitant was separated, and rinsed with MeOH and 20% EtOAc/hexane to yield 5-chloro-3-(5-dibenzylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow solid (36 mg, 23%).

Workup

  1. stirringthe reaction was rapidly stirred at room temperature for 1.5 hours
  2. customThe mixture was quenched into 4% HCl (20 ml)
  3. stirringstirred with EtOAc
  4. additionThe organic layer was diluted with MeOH
  5. additionfollowed by addition of HCl in MeOH
  6. customto give a yellow precipitant
  7. customThe yellow precipitant was separated
  8. washrinsed with MeOH and 20% EtOAc/hexane

Sources & evidence

ORD record
ord-0c038748f9554eeebb04771cdc69ca01
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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