Cesium carbonate → HCID 67036305, compound

HRID 1623432Notes

Reaction equation

HRID 1623432 reaction equation
[C:1]1([C:7](=[C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:24][O:23][C:21](=[O:22])[CH2:20][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[C:10]1=[O:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 23962083HCID 23962083, compound

Product 1

HCID 67036305HCID 67036305, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-Phenyl-ethylidene)-1,3-dihydro-indol-2-one (294 mg, 1 mmol) was dissolved in anhydrous DMF, then methyl bromoacetate (184 mg, 1.2 mmol) was added. Finally, Cs2CO3 (488 mg, 1.5 mmol) was added in one portion. The mixture was stirred at room temperature overnight. The reaction was monitored by HPLC. When the reaction was finished, the solvent was removed under reduced pressure. The residue was separated by flash chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether) to give [2-oxo-3-(1-phenyl-ethylidene)-2,3-dihydro-indol-1-yl]-acetic acid methyl ester as yellow powder (230 mg, 75%). MS calcd. for C19H17NO3 307, obsd. (ESI+) [(M+1)+] 308.1.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was separated by flash chromatography column (gradient elution, 5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d141b8c80e824849bb262dc5a1a76738
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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