Sodium Carbonate → Methyl 6-amino-3-bromopyridine-2-carboxylate

HRID 887754Notes

Reaction equation

HRID 887754 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:18]Br>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([Br:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 13809143Methyl 6-aminopyridine-2-carboxylate

Product 1

HCID 10657127Methyl 6-amino-3-bromopyridine-2-carboxylateYield 29.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of methyl 6-aminopyridine-2-carboxylate (5.98 g, 39.5 mmol) and sodium carbonate (2.64 g, 24.9 mmol) in acetic acid (150 mL) was added bromine (7.89 g, 49.4 mmol), and the mixture was stirred at room temperature for 7 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. This was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (2.67 g, yield 29%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialThis was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20)

Sources & evidence

ORD record
ord-7c14ce6f551f478f80413dbca7a96d0b
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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