N-bromobutanimide → 3-Bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde

HRID 2174068Notes

Reaction equation

HRID 2174068 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=[O:23].C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C.O>[Br:31][C:5]1[C:4]2[C:3]([CH:22]=[O:23])=[C:2]([CH3:1])[CH:10]=[C:9]([CH3:11])[C:8]=2[N:7]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86701532HCID 86701532, compound

Product 1

HCID 867016993-Bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (Example 46-D) (2 g, 6.11 mmol) in DMF (10 mL) was added NBS (2.39 g, 13.44 mmol), and then the mixture was stirred at 60° C. for 18.5 h. The reaction mixture was cooled to room temperature. The mixture was diluted with H2O, the layers were separated and the aqueous layer was extracted with EtOAc. The organic phase was washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel flash column chromatography to give the title compound. MS (ESI+) m/z 406.0, 408.0 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-b9093bf5ff504153bb1b5294beaa27b0
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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