N-Methyloxindole → HCID 14317864, compound

HRID 2200165Notes

Reaction equation

HRID 2200165 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13].Br[CH2:15][CH2:16]Br>CN(C=O)C>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2([CH2:16][CH2:15]2)[C:5]1=[O:13]

Participants

5

Reactant 3

HCID 6096N-MethyloxindoleHCID 78391,2-DibromoethaneHCID 24758Sodium hydride

Product 1

HCID 14317864HCID 14317864, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (60%, 1.4 g, 35.4 mmol) portionwise to the solution of 1-methylindolin-2-one (2.6 g, 17.7 mmol) in DMF (10 mL) at 0° C., stir for 30 min. Then add 1,2-dibromoethane (3.31 g, 17.7 mmol) to the mixture, stir the resulting mixture at room temperature overnight. Pour the reaction mixture to ice water, extract with ethyl acetate (100 mL×2), and wash the combined organic layers with brine (50 mL), dry over anhydrous sodium sulfate. Concentrate under reduced pressure, purify the residue by chromatography (silica gel, EtOAc:PE=1:3) to provide the title compound (1.5 g, 50.0%). MS: (M+1): 174.

Workup

  1. extractionextract with ethyl acetate (100 mL×2)
  2. washwash the combined organic layers with brine (50 mL)
  3. dry with materialdry over anhydrous sodium sulfate
  4. concentrationConcentrate under reduced pressure
  5. custompurify the residue by chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-a595977efe3147f2b7c0c7645a5ac724
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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