Dimethylformamide → 5-Iodo-6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]2[N:16]([CH:17]=1)[CH:15]=[CH:14][O:13]2.CN(C=O)C.C1C(=O)N([I:30])C(=O)C1>O>[I:30][C:17]1[N:16]2[C:12]([O:13][CH:14]=[CH:15]2)=[N:11][C:10]=1[C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[F:1]Participants
5
Procedure
To a round bottom flask containing 6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole (11.7 g, 49.1 mmol) and DMF (120 mL) was added NIS (11.4 g, 50.6 mmol). The reaction mixture was stirred at ambient temperature for about 1 h. The reaction mixture was poured into water (300 mL) and the resulting precipitate was collected by vacuum filtration. The solid was dissolved into DCM (500 mL) and the organic suspension was washed sequentially with saturated NaHCO3 solution, 5% sodium thiosulfate solution, and brine. The resulting solution was dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to give the title compound as a pale yellow solid (13.1 g, 73%): LC/MS (Table 1, Method b) Rt=2.17 min; MS m/z 365.0 (M+H)+.
Workup
- filtrationthe resulting precipitate was collected by vacuum filtration
- dissolutionThe solid was dissolved into DCM (500 mL)
- washthe organic suspension was washed sequentially with saturated NaHCO3 solution, 5% sodium thiosulfate solution, and brine
- dry with materialThe resulting solution was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-1106364313c84c05aaf47a6e42a78aca
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188083B2
Reaction notes
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