5-Chlorooxindole → 3-(5-Amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-one

HRID 1829005Notes

Reaction equation

HRID 1829005 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.C[Si](C)(C)N[Si](C)(C)C.[Na].[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:28](=O)[O:27][CH2:26]2>C(COC)OC.CN(C=O)C>[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:28](=[C:5]1[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][C:6]1=[O:11])[O:27][CH2:26]2

Participants

6

Reactant 3

HCID 1528015-ChlorooxindoleHCID 7206695-AminophthalideHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 696591863-(5-Amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-oneYield 31.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-chlorooxindole (0.629 g, 3.78 mmol) in 10.0 mL monoglyme was added 7.51 mL sodium hexamethyldisilazane (1.0 M in THF) over 3 min. After stirring at room temperature for 8 min, a solution of 5-aminophthalide (0.561 g, 3.78 mmol) in 3.0 mL of DMF was added over 1 min. The mixture was stirred for 40 min and then quenched into 4% aqueous HCl solution. The aqueous solution was neutralized to pH 7 with 1 M NaOH and then made basic with saturated NaHCO3. The solid was filtered and washed with H2O and then partitioned between EtOAc and saturated NaHCO3 (heated to dissolve the solid). The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the residue triturated with MeOH to give the title compound (353 mg, 31%) as a yellow solid.

Workup

  1. stirringThe mixture was stirred for 40 min
  2. customquenched into 4% aqueous HCl solution
  3. filtrationThe solid was filtered
  4. washwashed with H2O
  5. custompartitioned between EtOAc and saturated NaHCO3 (
  6. temperatureheated
  7. dissolutionto dissolve the solid)
  8. washThe organic phase was washed with H2O, brine
  9. dry with materialdried with Na2SO4
  10. customThe solvent was removed in vacuo
  11. customthe residue triturated with MeOH

Sources & evidence

ORD record
ord-c3e565af411e47c8b5a4b3d750696072
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

Loading…