Sodium hydride → HCID 86686559, compound

HRID 1528072Notes

Reaction equation

HRID 1528072 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[NH:6]2.[H-].[Na+].Br[CH2:20][CH:21]1[CH2:23][CH2:22]1.[Cl-].[NH4+]>CN(C=O)C>[CH:21]1([CH2:20][N:6]2[C:7]3[C:3](=[C:2]([F:1])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=3)[C:4]([CH3:16])([CH3:15])[C:5]2=[O:14])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 86686556HCID 86686556, compound

Product 1

HCID 86686559HCID 86686559, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-3,3-dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one (300 mg) in DMF (10 mL) were added sodium hydride (69.6 mg) and (bromomethyl)cyclopropane (0.193 mL) at 0° C., and the mixture was allowed to be warmed to room temperature, and stirred overnight under a nitrogen atmosphere. The reaction mixture was cooled to 0° C., saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (317 mg).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-84591d6445b3481a89b9a5aff5821365
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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