Bromoacetyl bromide → 2-bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanone

HRID 341280Notes

Reaction equation

HRID 341280 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:13][C:12]3[N:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:5]=2[CH:6]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl>[Br:18][CH2:19][C:20]([C:1]1[CH:6]=[C:5]2[C:4](=[CH:3][CH:2]=1)[NH:13][C:12]1[N:11]=[CH:10][CH:9]=[CH:8][C:7]2=1)=[O:21]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 674869H-Pyrido(2,3-b)indoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 585145292-bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanoneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0.2 M stirred suspension of the α-carboline derivative (200 mg) in anhydrous CH2Cl2 was added AlCl3 (4.5 equiv.) and bromoacetyl bromide (2.1 equiv.), at room temperature under inert atmosphere. The mixture was stirred at reflux until completion of the reaction (followed by t.l.c.). The resulting mixture was then cautiously quenched at 0° C. with H2O. It was extracted with the mixture of EtOAc/DMF (99:1). The resulting organic layer was washed with NaHCO3 saturated aqueous solution and brine, dried over MgSO4, filtered and solvents were removed under reduced pressure. 2-Bromo-1-(9H-pyrido[2,3-b]indol-6-yl)ethanone was obtained in 61% yield after trituration of the crude product in MeOH and filtration

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred
  3. temperatureat reflux until completion of the reaction (followed by t.l.c.)
  4. customThe resulting mixture was then cautiously quenched at 0° C. with H2O
  5. extractionIt was extracted with the mixture of EtOAc/DMF (99:1)
  6. washThe resulting organic layer was washed with NaHCO3 saturated aqueous solution and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customsolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-162228acfc8042b49d4148281349f85a
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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