Hydrochloric Acid → 5-bromo-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride

HRID 1661537Notes

Reaction equation

HRID 1661537 reaction equation
[ClH:1].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH2:12][CH3:13].Cl>C(O)C.O1CCOCC1>[ClH:1].[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:11]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[C:12]2[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 121574-Bromophenylhydrazine hydrochlorideHCID 740741-(3-Pyridyl)propan-1-one

Product 1

HCID 670931285-bromo-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 4-bromophenylhydrazine hydrochloride (10.00 g, 42.95 mmol) in anhydrous ethanol (200 mL) is added 3-propionylpyridine (7.51 g, 42.95 mmol) and the mixture is stirred at reflux for 30 min. 4M HCl in 1,4-dioxane (42.9 mL) is added to the yellow solution and stirring is continued at reflux overnight. The reaction mixture is cooled with an ice-water bath and the yellow precipitate is filtered through a sintered funnel to give 5-bromo-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride as a yellow solid. The product is dissolved in methanol (100 mL) and treated with sodium methoxide to give the free base, which is used in the next step without further purification.

Workup

  1. temperatureat reflux for 30 min
  2. stirringstirring
  3. temperatureat reflux overnight
  4. temperatureThe reaction mixture is cooled with an ice-water bath
  5. filtrationthe yellow precipitate is filtered through a sintered funnel

Sources & evidence

ORD record
ord-5cc331b33f164622b71cc95c266b079d
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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