Sodium hydride → 5-Bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethyl 2,2-dimethylpropionate

HRID 40483

Reaction equation

HRID 40483 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH3:13])[CH3:12].[H-].[Na+].[C:16]([O:22][CH2:23]Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[CH3:18][C:17]([CH3:20])([CH3:19])[C:16]([O:22][CH2:23][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[C:5]([CH3:13])([CH3:12])[C:6]1=[O:11])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 580317175-Bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethyl 2,2-dimethylpropionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of 5-bromo-3,3-dimethyl-1,3-dihydroindol-2-one was dissolved in 100 ml of dimethylformamide, and 217 mg of sodium hydride (60% dispersion in mineral oil) were added. The mixture was then stirred at room temperature for 30 minutes. Then the reaction mixture was cooled to 0° C. in an ice bath, and 941 mg of chloromethyl pivalate were added. The ice bath was removed and the reaction mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was diluted by adding 250 ml of ethyl acetate, and 50 ml of water were added. The organic phase was removed and washed once with 100 ml of saturated sodium chloride solution, dried over MgSO4 and then concentrated under reduced pressure. This gave 1.5 g of 5-bromo-3,3-dimethyl-2-oxo-2,3-dihydroindol-1-ylmethyl 2,2-dimethylpropionate.

Workup

  1. temperatureThen the reaction mixture was cooled to 0° C. in an ice bath
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  4. additionThen the reaction mixture was diluted
  5. additionby adding 250 ml of ethyl acetate, and 50 ml of water
  6. additionwere added
  7. customThe organic phase was removed
  8. washwashed once with 100 ml of saturated sodium chloride solution
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30420985f6444382afa7ed5065b6f1f2
Source dataset
uspto-grants-2013_09
Patent number
US08530413B2

Linked notes

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