N-bromobutanimide → Methyl 3-amino-6-bromo-5-fluoropicolinate

HRID 879138Notes

Reaction equation

HRID 879138 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C1C(=O)N([Br:20])C(=O)C1>C(#N)C>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([Br:20])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66652559Methyl 3-amino-5-fluoropicolinate

Product 1

HCID 72698878Methyl 3-amino-6-bromo-5-fluoropicolinateYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-amino-5-fluoropicolinate (1.0 equiv.) in acetonitrile (0.3 M solution) was added NBS (1.1 equiv.) for 2 minutes at room temperature. After quenched with water, the reaction mixture was extracted with EtOAc. The crude product was purified by silica column chromatography (20% to 50% EtOAc in hexanes) to give methyl 3-amino-6-bromo-5-fluoropicolinate (41%). LCMS (m/z): 249.1 (MH+); LC Rt=2.80 min.

Workup

  1. customAfter quenched with water
  2. extractionthe reaction mixture was extracted with EtOAc
  3. customThe crude product was purified by silica column chromatography (20% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-874608afb48b42a4932dd15926178a6e
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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