Hydrogen Bromide → [4-(5-Bromo-6-ethyl-3-methoxypyrazin-2-yl)-3-methoxyphenoxy]trifluoromethane

HRID 349185Notes

Reaction equation

HRID 349185 reaction equation
N([O-])=O.[Na+].[CH2:5]([C:7]1[C:8](N)=[N:9][C:10]([O:26][CH3:27])=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[O:24][CH3:25])[N:12]=1)[CH3:6].[BrH:29]>O.[Cu](Br)Br>[Br:29][C:8]1[N:9]=[C:10]([O:26][CH3:27])[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[O:24][CH3:25])=[N:12][C:7]=1[CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 222488983-Ethyl-6-methoxy-5-[2-methoxy4-(trifluoromethoxy)phenyl]pyrazin-2-ylamineHCID 23668193Sodium Nitrite

Product 1

HCID 22248930[4-(5-Bromo-6-ethyl-3-methoxypyrazin-2-yl)-3-methoxyphenoxy]trifluoromethane

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 962WaterSolvent

Procedure

A solution of sodium nitrite (21 mg, 0.3 mmol) in water (1 mL) is added to a stirred solution of 3-ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2ylamine (86 mg, 0.25 mmol) in 48% hydrogen bromide (0.3 mL) at 0 C. After 1.5 hours copper bromide (43 mg, 0.3 mmol) is added and the mixture heated to 70 C for 1 hour. 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-2yl)-3-methoxyphenoxy]trifluoromethane (76 mg).

Workup

  1. temperaturethe mixture heated to 70 C for 1 hour
  2. extractionextracted with ether
  3. dry with materialThe extracts are dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-567f0c4d17bb453398fde600410c22e7
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Reaction notes

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