Bromine → (2R)-4-(5-Bromo-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 912963Notes

Reaction equation

HRID 912963 reaction equation
[Br:1]Br.[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12][C@H:11]1[CH3:26])=[O:9])([CH3:6])([CH3:5])[CH3:4]>ClCCl>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:21]([C:22]([F:25])([F:23])[F:24])=[CH:20][C:19]([Br:1])=[CH:18][N:17]=2)[CH2:12][C@H:11]1[CH3:26])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 11523056(2R)-2-Methyl-4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11575439(2R)-4-(5-Bromo-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (1.52 mL, 29.7 mmol, Aldrich) was added dropwise over a period of 5 min to a solution (2R)-2-methyl-4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester from step (b) above (9.34 g, 27 mmol) in dichloromethane (100 mL) with stirring at room temperature. The mixture was stirred at room temperature for 30 min, the solvent was removed in vacuo and the residue was dissolved in EtOAc (200 mL). The solution was washed with sat. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 10% EtOAc/hexane to give the title compound as a gum. MS (ESI, pos. ion) m/e: 426 (M+1).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (200 mL)
  4. washThe solution was washed with sat. NaHCO3 (50 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography
  9. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-ae1fe33e43464b11b4e89b3df1c9f279
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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