N-bromobutanimide → HCID 58368367, compound

HRID 1851086Notes

Reaction equation

HRID 1851086 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:11]=1[O:12][C:13]1[C:14]2[N:15]([CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:17][CH:18]=1>C(Cl)(Cl)Cl>[Br:1][C:21]1[CH:20]=[CH:19][N:15]2[C:14]=1[C:13]([O:12][C:11]1[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:10]=1[F:9])=[CH:18][CH:17]=[N:16]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 587990064-(2-Fluoro-4-nitrophenoxy)pyrrolo[1,2-b]pyridazine

Product 1

HCID 58368367HCID 58368367, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (1.49 g, 8.42 mmol) was added to a solution of 4-(2-fluoro-4-nitrophenoxy)pyrrolo[1,2-b]pyridazine (2.30 g, 8.42 mmol) in anhydrous chloroform (70 mL) at 0° C. and stirred for 4 hours. Upon completion of the reaction, the resulting mixture was washed by adding water thereto. The organic layer was separated, dried with magnesium sulfate, and then filtered. The filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to give the target compound as a yellow solid (840 mg, 2.39 mmol, 28% yield).

Workup

  1. customUpon completion of the reaction
  2. washthe resulting mixture was washed
  3. additionby adding water
  4. customThe organic layer was separated
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated by distillation under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-67741b83f5514665974ad1a81ba1a5cf
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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