2-Bromopropane → HCID 86686574, compound

HRID 1528092Notes

Reaction equation

HRID 1528092 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:16])([CH3:15])[C:5](=[O:14])[NH:6]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:24]([CH3:26])[CH3:25].[Cl-].[NH4+]>CN(C=O)C>[NH2:11][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[N:6]([CH:24]([CH3:26])[CH3:25])[C:5](=[O:14])[C:4]2([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 86686556HCID 86686556, compound

Product 1

HCID 86686574HCID 86686574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-fluoro-3,3-dimethyl-5-nitro-1,3-dihydro-2H-indol-2-one (500 mg) and cesium carbonate (1.82 g) in DMF (10 mL) was added dropwise 2-bromopropane (0.523 mL) at room temperature, and the mixture was stirred at 80° C. for 2 hr under a nitrogen atmosphere. To the reaction mixture was added saturated aqueous ammonium chloride solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in ethanol (10 mL), palladium on carbon (containing water (50%), 237 mg) was added thereto, and the mixture was stirred at room temperature for 2 hr under a hydrogen atmosphere. The palladium on carbon was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (330 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in ethanol (10 mL)
  6. additionpalladium on carbon (containing water (50%), 237 mg) was added
  7. stirringthe mixture was stirred at room temperature for 2 hr under a hydrogen atmosphere
  8. customThe palladium on carbon was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f50f2ef296fb40c98aaf496192005f1c
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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