N-bromobutanimide → 1-(2,4-Difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethane-1,2-dione

HRID 1929988Notes

Reaction equation

HRID 1929988 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:23])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([CH:20]([CH3:22])[CH3:21])=[N:18][N:19]=2)[N:16]=1.C1C(=O)N(Br)C(=[O:27])C1>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:23])[C:10]([C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([CH:20]([CH3:21])[CH3:22])=[N:18][N:19]=2)[N:16]=1)=[O:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 579298581-(2,4-Difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 579298591-(2,4-Difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethane-1,2-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a round bottom flask was added 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (1.50 g, 4.74 mmol, Preparation #K.1) followed by DMSO (15 mL) and NBS (0.844 g, 4.74 mmol). The reaction mixture was stirred at about ambient temperature for about 3 d. The reaction mixture was partitioned between EtOAc and water. The layers were separated, and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using heptane/EtOAc (gradient, 1:0 to 0:1) to give the title compound (1.14 g, 73%): LC/MS (Table 1, Method a) Rt=2.4 min; MS m/z: 331.1 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7655f61979204d7aaf1fef231c13e2ba
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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