N-bromobutanimide → 3-bromo-9-(2-pyridinyl)-9H-Carbazole

HRID 716596Notes

Reaction equation

HRID 716596 reaction equation
[Br:1]N1C(=O)CCC1=O.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2>CN(C=O)C.C1COCC1>[Br:1][C:24]1[CH:25]=[CH:26][C:27]2[N:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 101017639-(pyridin-2-yl)-9H-carbazole

Product 1

HCID 675167383-bromo-9-(2-pyridinyl)-9H-Carbazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-bromosuccinimide (17.8 g, 100 mmol) in DMF (50 mL) was added slowly to 9-(pyridin-2-yl)-9H-carbazole (24 g, 100 mmol) in THF (250 mL) at 0° C. over 30 min. The reaction was allowed to warm to room temperature and stir overnight. The reaction mixture was then evaporated and extracted with dichloromethane, and the organic layer was dried over magnesium sulfate and the solvent was then evaporated. The residue was then purified by column using toluene:hexane (1:1, v/v) as eluent and the product was further purified by recrystallization from toluene:ethanol (1:1, v/v), and after cooling, 24.3 g (75%) of the product was collected as a white solid after filtration.

Workup

  1. customThe reaction mixture was then evaporated
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customthe solvent was then evaporated
  5. customThe residue was then purified by column
  6. customv/v) as eluent and the product was further purified by recrystallization from toluene:ethanol (1:1
  7. temperaturev/v), and after cooling
  8. custom24.3 g (75%) of the product was collected as a white solid
  9. filtrationafter filtration

Sources & evidence

ORD record
ord-851d6f8eff904af0b96378e42a6ac6f6
Source dataset
uspto-grants-2015_11
Patent number
US09190623B2

Reaction notes

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