5-chloro-1H-indole-2,3-dione → HCID 21905920, compound

HRID 1243323Notes

Reaction equation

HRID 1243323 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]([F:12])([F:11])[F:10].[Mg].[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:18]2=[O:25]>CCOCC.C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=[O:24])[C:18]2([OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]([F:12])([F:11])[F:10]

Participants

6

Reactant 3

HCID 872035-chloro-1H-indole-2,3-dioneHCID 27772661-Bromo-2-(trifluoromethoxy)benzeneHCID 5462224Magnesium

Product 1

HCID 21905920HCID 21905920, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25 g of 1-bromo-2-trifluoromethoxybenzene in 130 ml of ether is added dropwise to a mixture of 2.8 g of magnesium in 20 ml of ether, the reflux being maintained once it has started. At the end of the addition, the mixture is heated at reflux for one hour. A mixture of 7.5 g of 5-chloro-1H-indole-2,3-dione in 100 ml of THF is then added, at a temperature below 40° C., followed by refluxing for one hour. After cooling to RT, the reaction mixture is poured into an ice/concentrated HCl mixture and extracted with EtOAc, the organic phase is washed with water, with 1N NaOH solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 6.5 g of the expected product are obtained after crystallization from a DCM/iso ether mixture (20/80; v/v),

Workup

  1. temperaturethe reflux being maintained once it
  2. additionAt the end of the addition
  3. temperaturethe mixture is heated
  4. temperatureat reflux for one hour
  5. additionis then added, at a temperature below 40° C.
  6. temperatureby refluxing for one hour
  7. extractionextracted with EtOAc
  8. washthe organic phase is washed with water, with 1N NaOH solution
  9. dry with materialdried over Na2SO4
  10. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-f32a143476a94bc4a9881a98c7a3eddc
Source dataset
uspto-grants-2006_10
Patent number
US07119086B2

Reaction notes

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