Bromine → Tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylate

HRID 2403611Notes

Reaction equation

HRID 2403611 reaction equation
[CH:1]([C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1)=[O:2].[Br:22]Br>C(O)(=O)C>[Br:22][C:7]1[CH:8]=[C:3]([CH:1]=[O:2])[C:4]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 24741846tert-Butyl 4-(3-formylpyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86667973Tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylateYield 85.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

tert-Butyl 4-(3-formylpyridin-2-yl)piperazine-1-carboxylate (1.88 g) was dissolved in acetic acid (20 ml), and bromine (1.03 g) was added dropwise thereto, followed by stirring at room temperature for 30 minutes. The solvent was evaporated under reduced pressure. The obtained residue was subjected to liquid separation by the addition of CHCl3 and a 1 M aqueous NaOH solution. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl 4-(5-bromo-3-formylpyridin-2-yl)piperazine-1-carboxylate (2.05 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe obtained residue was subjected to liquid separation by the addition of CHCl3
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7c00c3c7fd14f74b1487e90acee8a11
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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