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

HRID 1711784Notes

Reaction equation

HRID 1711784 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.O>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])[CH:14]=[CH:13][O:12]2

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 594578706-(2,4-Difluorophenyl)imidazo[2,1-b]oxazole2×

Product 1

HCID 594578066-(2,4-Difluorophenyl)-5-iodoimidazo[2,1-b]oxazoleYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a round bottom flask charged with 6-(2,4-difluorophenyl)-imidazo[2,1-b]oxazole (5.0 g, 23 mmol; prepared using A from 6-(2,4-difluorophenyl)-imidazo[2,1-b]oxazole [prepared according to WO2004110990A2, Example 1, Steps 1-3 using 2-bromo-1-(2,4-difluorophenyl)-ethanone in place of 2-bromo-1-(4-fluorophenyl)-ethanone]) and DMF (100 mL) was added a solution of NIS (5.4 g, 24 mmol) in DMF (20 mL) at ambient temperature. The reaction was allowed to stir at ambient temperature for about 1 h upon which time it was poured into water (800 mL). The resulting precipitate was filtered, washed with water (2×20 mL), and dried in a vacuum oven for about 16 h to provide the title compound (7.5 g, 95%) as a light yellow solid: LC/MS (Table 1, Method a) Rt=2.04 min; MS m/z/z: 347.0 (M+H)+.

Workup

  1. customprepared
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (2×20 mL)
  4. customdried in a vacuum oven for about 16 h

Sources & evidence

ORD record
ord-5e5bd099109d4d0b83ce15e97a2af504
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

Loading…