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

HRID 1581709Notes

Reaction equation

HRID 1581709 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, and once the refluxing has started it is maintained. At the end of the addition the mixture is refluxed for 1 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 1 hour. After cooling to RT, the reaction mixture is poured into an ice/concentrated HCl mixture, the resulting mixture is extracted with EtOAc, the organic phase is washed with water, with 1N NaOH solution and dried over Na2SO4, and the solvent is evaporated 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. temperatureis maintained
  2. additionAt the end of the addition the mixture
  3. temperatureis refluxed for 1 hour
  4. additionis then added, at a temperature below 40° C.
  5. temperatureby refluxing for 1 hour
  6. extractionthe resulting mixture is extracted with EtOAc
  7. washthe organic phase is washed with water, with 1N NaOH solution
  8. dry with materialdried over Na2SO4
  9. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-efb436673de6408295ba59ddb6452a09
Source dataset
uspto-grants-2004_05
Patent number
US06730695B2

Reaction notes

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