Water → HCID 18520399, compound

HRID 1368771Notes

Reaction equation

HRID 1368771 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].O>CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]2[CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 24758Sodium hydrideHCID 15370496Ethyl 6-fluoro-1H-indole-2-carboxylate

Product 1

HCID 18520399HCID 18520399, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 1.0 g portion of ethyl 6-fluoro-2-indolecarboxylate was dissolved in 50 ml of dimethylformamide, mixed under ice-cooling with a suspension consisting of 0.3 g of 60% sodium hydride and 10 ml of dimethylformamide, stirred at the same temperature for 30 minutes, further mixed with 5.0 g of N-(2-bromoethyl)phthalimide and then stirred for 24 hours while gradually returning to room temperature. After terminating the reaction by adding water, this was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was evaporated. The thus obtained residue was applied to a silica gel column chromatography and developed with a hexane-ethyl acetate (9:1) mixed solvent, thereby obtaining 0.74 g of the title compound.

Workup

  1. additionmixed under ice-
  2. temperaturecooling with a suspension
  3. stirringstirred for 24 hours
  4. customwhile gradually returning to room temperature
  5. customAfter terminating
  6. customthe reaction
  7. extractionthis was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried with anhydrous sodium sulfate
  10. customthe solvent was evaporated
  11. additionmixed solvent

Sources & evidence

ORD record
ord-b4c25ec53c1147af886b6f4668afb587
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

Loading…