Hydrochloric Acid → 6-Bromo-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 1507575Notes

Reaction equation

HRID 1507575 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.Br[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[C:7](=[O:11])[N:8]2[CH:15]([CH3:17])[CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 106576496-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 900463286-Bromo-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 6-bromo-3,3-dimethylindolin-2-one (example 14a, 1.68 g, 7.00 mmol) in DMF (30 ml) were added 2-bromopropane (2.15 g, 1.64 ml, 17.5 mmol) and cesium carbonate (5.02 g, 15.4 mmol). The reaction mixture was heated to 80° C. for 18 hours. The reaction mixture was treated with 1 M HCl and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as orange solid (2.00 g, 70% purity) and was used for the next reaction without further purification.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ad75f22fd8cd446d9994b117f46ea06b
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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