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

HRID 983524Notes

Reaction equation

HRID 983524 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 refluxed 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 and 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); m.p.=214° C.

Workup

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

Sources & evidence

ORD record
ord-30279d1aa4e649b291e7374efb85a39e
Source dataset
uspto-grants-2005_03
Patent number
US06864277B2

Reaction notes

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