Hydrogen Bromide → 5-Chloro-8-iodoimidazo[1,2-a]pyridine
Reaction equation
[NH2:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.Br.[CH:11](O)(C)[CH3:12]>>[Cl:9][C:4]1[N:3]2[CH:11]=[CH:12][N:1]=[C:2]2[C:7]([I:8])=[CH:6][CH:5]=1Participants
4
Procedure
2-amino-3-iodo-6-chloropyridine (2 g, 7.874 mmol) is taken up in isopropanol (30 mL) under N2. Diethoxy-2-bromoacetal (2.5 mL, 15.748 mmol, 2 equiv.) is added to the suspension followed by HBr 48% (2 mL). The resulting mixture is then refluxed for 12 h and cooled down to room temperature. The mixture is partly concentrated under vacuum and the resulting slurry is taken up in diethyl ether which causes the precipitation of a solid that is separated by filtration and washed with little amounts of diethyl ether to afford the desired material as a powder.
Workup
- temperatureThe resulting mixture is then refluxed for 12 h
- concentrationThe mixture is partly concentrated under vacuum
- customthe precipitation of a solid
- customthat is separated by filtration
- washwashed with little amounts of diethyl ether
Sources & evidence
- ORD record
- ord-3a874d3d80434a5181dc478c859ef173
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951818B2
Reaction notes
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