Potassium Iodide → Benzyl N-(2-oxo-2,3-dihydro-1H-indol-4-yl)glycinate

HRID 1097432Notes

Reaction equation

HRID 1097432 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.Br[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C=O)C>[O:11]=[C:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[NH:1][CH2:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[NH:6]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 122374724-Aminoindolin-2-one

Product 1

HCID 66813100Benzyl N-(2-oxo-2,3-dihydro-1H-indol-4-yl)glycinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-amino-1,3-dihydro-2H-indol-2-one (300 mg, 2.03 mmol), benzyl bromoacetate (0.32 mL, 2.03 mmol), cesium carbonate (660 mg, 2.03 mmol), and potassium iodide (336 mg, 2.03 mmol) in DMF (10 mL) was stirred at 50° C. for 4 h. The cooled reaction mixture was quenched with H2O (10 mL) and extracted with EtOAc (2×15 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=297 (M+1).

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched with H2O (10 mL)
  3. extractionextracted with EtOAc (2×15 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-5df8d1bb8a13430eae1f1734bafcf07b
Source dataset
uspto-grants-2012_03
Patent number
US08143266B2

Reaction notes

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