Sodium hydride → HCID 23120690, compound

HRID 490149Notes

Reaction equation

HRID 490149 reaction equation
[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[H-].[Na+].Br[Mg][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[O:25][CH3:26].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[O:25][CH3:26])[OH:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23120703HCID 23120703, compoundHCID 178490716HCID 178490716, compound

Product 1

HCID 23120690HCID 23120690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.96 g of 5-chloro-4-methyl-1H-indol-2,3-dione was added under ice cooling and a nitrogen atmosphere to a 50 mL tetrahydrofuran solution of 440 mg of sodium hydride, and the reaction mixture was stirred for 1 hour. After this, a previously prepared 15 mL tetrahydrofuran solution of bromo(5-chloro-2-methoxyphenyl)magnesium was added dropwise over a period of 10 minutes. The reaction mixture was stirred for 3 hours at the same temperature, after which 50 mL of a saturated ammonium chloride aqueous solution was added, and the reaction mixture was stirred for another 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (30 mL×3), and the combined organic layer was washed with saturated brine and dried with sodium sulfate, and the drying agent was then filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was stirred and washed with isopropyl ether, and the solids were then filtered off to obtain 2.43 g of the titled compound (yellow solid).

Workup

  1. stirringthe reaction mixture was stirred for another 30 minutes at room temperature
  2. customAfter liquid separation
  3. extractionthe aqueous layer was extracted with ethyl acetate (30 mL×3)
  4. washthe combined organic layer was washed with saturated brine
  5. dry with materialdried with sodium sulfate
  6. filtrationthe drying agent was then filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue thus obtained
  9. stirringwas stirred
  10. washwashed with isopropyl ether
  11. filtrationthe solids were then filtered off

Sources & evidence

ORD record
ord-318c7014e29c45af923f778b0cfc652b
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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