Water → Ethyl (3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

HRID 913181Notes

Reaction equation

HRID 913181 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14](O)=[C:13]3[CH:19]=[CH:20][CH:21]=[CH:22][C:12]3=[C:11]([O:23][CH2:24][CH3:25])[C:10]=2[C:9]1=[O:26].C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)S([O:44][CH2:45][C:46]([F:49])([F:48])[F:47])(=O)=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:44][CH2:45][C:46]([F:49])([F:48])[F:47])=[C:13]3[CH:19]=[CH:20][CH:21]=[CH:22][C:12]3=[C:11]([O:23][CH2:24][CH3:25])[C:10]=2[C:9]1=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 58012488Ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate

Product 1

HCID 58012482Ethyl (3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetateYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate (0.60 g, 1.32 mmol) in DMF (6 ml), was added sodium carbonate (0.280 g, 2.65 mmol) followed by 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.460 g, 1.98 mmol). This was stirred at room temperature for 5 hours. Water was added to the reaction mixture and the resulting brown solid was collected by filtration. This was purified by chromatography on silica gel eluting with 5-60% ethylacetate in hexane to give the title compound (0.258 g, 0.48 mmol). LC/MS: Rt=3.85, [MH]+ 536.

Workup

  1. filtrationthe resulting brown solid was collected by filtration
  2. customThis was purified by chromatography on silica gel eluting with 5-60% ethylacetate in hexane

Sources & evidence

ORD record
ord-48151cac0d8a4db383a6d756a1ea6caf
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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