Water → 3-Bromo-7-[(2-chloro-4-fluorophenyl)carbonyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 1893426Notes

Reaction equation

HRID 1893426 reaction equation
[Cl:1][C:2]1[C:7]([C:8](F)([F:10])F)=C[CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]2[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=[C:16]2[CH2:15]1)=O.C1C(=O)N([Br:34])C(=O)C1.[OH2:35].S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Br:34][C:20]1[N:17]2[CH2:18][CH2:19][N:14]([C:12]([C:3]3[CH:4]=[CH:5][C:8]([F:10])=[CH:7][C:2]=3[Cl:1])=[O:35])[CH2:15][C:16]2=[N:22][C:21]=1[C:23]([F:25])([F:26])[F:24]

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 497850117-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Product 1

HCID 497853723-Bromo-7-[(2-chloro-4-fluorophenyl)carbonyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (I22) (181 mg, 0.455 mmol) was dissolved in N,N-dimethylformamide (DMF) (2 mL) and treated with NBS (97 mg, 0.546 mmol). The solution was stirred at RT for 16 h. The mixture was poured on to water (100 ml) containing 1% sodium sulfite (w/w) and extrated in to ethyl acetate (3×50 ml). Combined extracts were washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated to afford crude product. The crude product was purified by MDAP to afford desired product in 135 mg.

Workup

  1. washCombined extracts were washed with brine (50 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto afford crude product
  5. customThe crude product was purified by MDAP

Sources & evidence

ORD record
ord-ea9dd6c2c7a24d3aadbdb9f88f0a3a50
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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