Hydrogen Bromide → [4-(5-Bromo-6-ethyl-3-methoxypyrazin-2-yl)-3-methoxyphenoxy]trifluoromethane
Reaction equation
[CH2:1]([C:3]1[C:4](N)=[N:5][C:6]([O:22][CH3:23])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[O:20][CH3:21])[N:8]=1)[CH3:2].N([O-])=O.[Na+].[BrH:29]>O.[Cu](Br)Br>[Br:29][C:4]1[N:5]=[C:6]([O:22][CH3:23])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[O:20][CH3:21])=[N:8][C:3]=1[CH2:1][CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a stirred solution of 3-ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy) phenyl]pyrazin-2-ylamine (86 mg, 0.25 mmol) in 48% hydrogen bromide (0.3 mL) at 0° C. is added a solution of sodium nitrite (21 mg, 0.3 mmol) in water (1 mL). After 1.5 h copper bromide (43 mg, 0.3 mmol) is added and the mixture heated to 70° C. for 1 h. The mixture is cooled to room temperature and extracted with ether. The extracts are dried (sodium sulfate), filtered and concentrated to give [4-(5-bromo-6-ethyl-3-methoxypyrazin-2-yl)-3-methoxyphenoxy]trifluoromethane (76 mg).
Workup
- temperatureThe mixture is cooled to room temperature
- extractionextracted with ether
- dry with materialThe extracts are dried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3d743e7b6a3345fc9a2260b15c1b832b
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995161B2
Reaction notes
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