HCID 131733468, compound → 4-bromo-5-methyl-1H-indole

HRID 2278389Notes

Reaction equation

HRID 2278389 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([N+]([O-])=O)[C:3]=1[CH:12]=[CH:13][N:14](C)C>CC(O)=O.O.O.[Zn]>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[CH:12]=[CH:13][NH:14]2

Participants

5

Reactant 1

HCID 131733468HCID 131733468, compound

Product 1

HCID 104886354-bromo-5-methyl-1H-indoleYield 20%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

[2-(2-Bromo-3-methyl-6-nitro-phenyl)vinyl]-dimethyl-amine (10 g) was dissolved in AcOH/H2O (100 mL:25 mL), cooled to 0° C. and treated with Zn (30 g) added slowly in portions. After complete addition, the reaction mixture was heated at 110° C. overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to afford the title compound (1.4 g, 20%)

Workup

  1. additionadded slowly in portions
  2. additionAfter complete addition
  3. temperaturethe reaction mixture was heated at 110° C. overnight
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3321f709d204f7b9870ba989000862c
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

Loading…