N-Iodosuccinimide → HCID 57929914, compound

HRID 1929968Notes

Reaction equation

HRID 1929968 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([CH:16]=1)[CH2:14][CH2:13][O:12]2.C1C(=O)N([I:24])C(=O)C1>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[I:24])[CH2:14][CH2:13][O:12]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 57929898HCID 57929898, compound

Product 1

HCID 57929914HCID 57929914, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 6-(2,4-difluorophenyl)-2,3-dihydroimidazo[2,1-b]oxazole (0.500 g, 2.25 mmol) was dissolved in DMF (6 mL) then NIS (0.533 g, 2.25 mmol) was added in one portion. The mixture was stirred at ambient temperature for about 15 min. The solvent was removed under reduced pressure then the residue was dissolved in DCM (6 mL) and purified by flash chromatography on silica gel using DCM/EtOAc (1:1) as an eluent. The desired fractions were combined and concentrated under reduced pressure to give a brown solid that was then triturated with water (10 mL). The solid was collected by filtration then dried under vacuum at about 70° C. for about 12 h to give the title compound (0.635 g, 81%): LC/MS (Table 1, Method h) Rt=1.39 min; MS m/z: 349 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (6 mL)
  3. custompurified by flash chromatography on silica gel
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown solid that
  6. customwas then triturated with water (10 mL)
  7. filtrationThe solid was collected by filtration
  8. customthen dried under vacuum at about 70° C. for about 12 h

Sources & evidence

ORD record
ord-b4cab9c207bc47b7895596a9dee7f47b
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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