Phthalide → 3-(2-Benzofuran-1(3H)-ylidene)-5-fluoro-1,3-dihydro-2H-indol-2-one

HRID 1828993Notes

Reaction equation

HRID 1828993 reaction equation
[F: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:12]1([C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1)=O.C[Si](C)(C)N[Si](C)(C)C.[Na]>CN(C=O)C>[F: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:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][O:14]1

Participants

5

Reactant 3

HCID 6885PhthalideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 696593963-(2-Benzofuran-1(3H)-ylidene)-5-fluoro-1,3-dihydro-2H-indol-2-oneYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution at 0° C. containing 5-fluorooxindole (0.30 g, 1.99 mmol) and phthalide (0.400 g, 2.98 mmol) in 5.0 mL DMF was added 4.2 mL of sodium hexamethyldisilazane (1.0 M in THF) over 5 min. The solution was stirred at room temperature for 3 h and then quenched into cold 1.0 M aqueous HCl solution to give a yellow solid. The solid was collected and then purified by chromatography (silica gel, hexanes/EtOAc, 4:1) to afford the title compound (32 mg, 6%) as a yellow solid.

Workup

  1. customquenched into cold 1.0 M aqueous HCl solution
  2. customto give a yellow solid
  3. customThe solid was collected
  4. custompurified by chromatography (silica gel, hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-11db883cd44b4b899fb85fda3f4fafe4
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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