Dimethylformamide → 6-(2,4-Difluorophenyl)-5-iodoimidazo[2,1-b]oxazole

HRID 1929973Notes

Reaction equation

HRID 1929973 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)[CH:14]=[CH:13][O:12]2.C1C(=O)N([I:24])C(=O)C1.CN(C=O)C>O>[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])[CH:14]=[CH:13][O:12]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 594578706-(2,4-Difluorophenyl)imidazo[2,1-b]oxazole

Product 1

HCID 594578066-(2,4-Difluorophenyl)-5-iodoimidazo[2,1-b]oxazoleYield 73.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole (30.0 g, 136 mmol; Example #8, step B), NIS (31.6 g, 140 mmol), and DMF (350 mL) was stirred at ambient temperature. After about 1 h, the reaction was poured into water (2 L) and the resulting precipitate was filtered and washed with additional water. The brown solid was dissolved in DCM and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to dryness. The solid was dissolved in DCM, filtered through Florosil® and then concentrated under reduced pressure to a volume of about 0.5 L. The organic layer was washed with 5% aqueous NaS2O3, dried over MgSO4, filtered, and concentrated under reduced pressure to dryness to give the title compound as a yellow solid (34.5 g, 73%): LC/MS (Table 1, Method a) Rt=2.67 min; MS m/z: 346.9 (M+H)+.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with additional water
  3. dissolutionThe brown solid was dissolved in DCM
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to dryness
  8. dissolutionThe solid was dissolved in DCM
  9. filtrationfiltered through Florosil®
  10. concentrationconcentrated under reduced pressure to a volume of about 0.5 L
  11. washThe organic layer was washed with 5% aqueous NaS2O3
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-7f4cf0c2edd74391a5aced5fd6c850b5
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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