Potassium Carbonate → HCID 86681664, compound

HRID 571250Notes

Reaction equation

HRID 571250 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 362195-NitroindolineHCID 62576Benzyl bromoacetate

Product 1

HCID 86681664HCID 86681664, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-nitroindoline (1 g, 6.09 mmol) in dry DMF (20 ml), K2CO3 (1.094 g, 7.92 mmol) and benzyl 2-bromoacetate (1.242 ml, 7.92 mmol) were added, and the resulting suspension was heated at 65° C. for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was removed. The residue was purified by flash chromatography on silica gel column (DCM:petroleum ether=60:40) affording benzyl 2-(5-nitroindolin-1-yl)acetate (0.782 g, 2.504 mmol, 41% yield). MS/ESI+ 312.9 [MH]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by flash chromatography on silica gel column (DCM:petroleum ether=60:40)

Sources & evidence

ORD record
ord-f740738d433240749b8579cce62ead16
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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