Oxindole → HCID 69662062, compound

HRID 1829058Notes

Reaction equation

HRID 1829058 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:21][N:22]([CH2:24][CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=O)[O:26]1)[CH3:23].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>C(COC)OC.C1COCC1>[CH3:23][N:22]([CH2:24][CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[O:26]1)[CH3:21]

Participants

7

Reactant 4

HCID 321710OxindoleHCID 2733832Lithium HexamethyldisilazideHCID 220615043-[(Dimethylamino)methyl]-2-benzofuran-1(3H)-oneHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 69662062HCID 69662062, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of oxindole (205 mg, 1.54 mmol) in dimethoxyethane (4.0 ml) at room temperature was added 1.0M LiHMDS in THF (1.54 ml). After stirring for 10 minutes at room temperature, 3-dimethylaminomethyl-3H-isobenzofuran-1-one (235 mg, 1.23 mmol) in dimethoxyethane (0.5 ml) was added and the mixture was stirred rapidly for 1 hour. Additional 1.0M LiHMDS/THF (1.54 ml) was added. After 2 hours the reaction was quenched into 10% HCl (50 ml) and 25 ml water added. The aqueous layer was washed with EtOAc and then basified with saturated NaHCO3 aqueous solution. The aqueous layer was extracted with EtOAc. The EtOAc layer was washed with brine, dried over anhydrous Na2SO4, and rotary evaporated to provide a yellow solid. The yellow solid was chromatographed silica gel column (CHCl3 to 2.5% MeOH/CHCl3 gradient) and then recrystallized from MeOH to give 3-(3-dimethylaminomethy-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as yellow needles (92 mg, 24%).

Workup

  1. stirringthe mixture was stirred rapidly for 1 hour
  2. customAfter 2 hours the reaction was quenched into 10% HCl (50 ml) and 25 ml water
  3. additionadded
  4. washThe aqueous layer was washed with EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washThe EtOAc layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customrotary evaporated
  9. customto provide a yellow solid
  10. customThe yellow solid was chromatographed silica gel column (CHCl3 to 2.5% MeOH/CHCl3 gradient)
  11. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-b5f848af52d845f6b7f939f1b275e9ee
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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