Pyridiniumtribromide → 2-Bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

HRID 1929970Notes

Reaction equation

HRID 1929970 reaction equation
[Br-:1].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C:30](=[O:44])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]2[N:36]([C:38]([CH:41]([CH3:43])[CH3:42])=[N:39][N:40]=2)[N:37]=1>C1COCC1.C(Cl)Cl>[Br:1][CH:31]([C:32]1[CH:33]=[CH:34][C:35]2[N:36]([C:38]([CH:41]([CH3:42])[CH3:43])=[N:39][N:40]=2)[N:37]=1)[C:30]([C:24]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=1[F:22])=[O:44]

Participants

5

Reactant 2

HCID 21124087PyridiniumtribromideHCID 579298581-(2,4-Difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 579298612-Bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanoneYield 100.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridinium tribromide (0.567 g, 1.77 mmol) was added to a solution of 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.488 g, 1.54 mmol; Preparation #K.1) in THF (6 mL) and the resulting reaction mixture was stirred at ambient temperature for about 4 h. The crude mixture was diluted with DCM (20 mL) and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude title compound (0.61 g, 100%): LC/MS (Table 1, Method a) Rt=3.28 min; MS m/z: 396.9 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. washwashed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-058d16031a0a413faf454bac0c29f167
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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