Isoamyl Nitrite → 4-Bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[C:4](N)[CH:3]=1.C(ON=O)CC(C)C.C[Si](C)(C)[Br:25]>BrCBr>[Br:25][C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11]Participants
5
Procedure
To a suspension of 2.30 g 6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazin-4-ylamine in 23 mL dibromomethane was added 5.11 g isoamylnitrite at once and drop wise 4.642 g trimethylbromosilane at ambient temperature (during ca 10 min). A moderate exotherm was observed and a dark brown solution was obtained. The mixture was stirred at ambient temperature for 18 h. The solvents were evaporated and the residue was purified (3×) by chromatography on silica gel using a gradient of heptane to dichloromethane to yield 0.70 g of the title compound as white crystalline solid, MS 292 (M+H)+.
Workup
- customat ambient temperature
- custom(during ca 10 min)
- customa dark brown solution was obtained
- customThe solvents were evaporated
- customthe residue was purified (3×) by chromatography on silica gel using a gradient of heptane to dichloromethane
Sources & evidence
- ORD record
- ord-5fbbd08d08c34af1a9aadc4b584b9485
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729105B2
Reaction notes
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