2,4,5-Trifluorobenzyl Bromide → HCID 69366630, compound

HRID 1295698Notes

Reaction equation

HRID 1295698 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15](=[O:20])[NH:16][CH:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].[F:27][C:28]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:29]=1[CH2:30]Br>C1COCC1>[F:27][C:28]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:29]=1[CH2:30][N:16]1[CH:17]=[CH:18][N:19]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[C:15]1=[O:20]

Participants

5

Reactant 3

HCID 27770572,4,5-Trifluorobenzyl BromideHCID 23665647Potassium tert-butoxideHCID 590138923-(4-tert-Butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone

Product 1

HCID 69366630HCID 69366630, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-tert-butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone (obtained in Step 1 above; 1.30 g, 4.66 mmol) in THF (20 mL) was added t-BuOK (0.53 g, 4.66 mmol) and the mixture was stirred at room temperature for 10 min. The resulting solution was added dropwise to a stirred solution of 2,4,5-trifluorobenzyl bromide (1.20 g, 5.33 mmol) in THF (20 mL) at room temperature. After 2 h, the reaction mixture was cooled to 0° C. and partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was washed with brine (10 mL) and dried over Na2SO4. Evaporation of the solvent gave 1.82 g (96%) of the title compound as an oil which crystallized upon standing. The product can be recrystallized from tert-butyl methyl ether. HPLC purity: 94%. 1NMR and MS analyses support the stated structure.

Workup

  1. waitAfter 2 h
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. custompartitioned between water (20 mL) and EtOAc (50 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3803f327a8ec48d99c5da8ff69a36407
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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