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

HRID 1499433Notes

Reaction equation

HRID 1499433 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.[Br:13]N1C(=O)CCC1=O>CC#N.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([Br:13])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

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

Product 1

HCID 72698878Methyl 3-amino-6-bromo-5-fluoropicolinateYield 76.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-amino-5-fluoropyridine-2-carboxylate (3.6 g, 21 mmol) in MeCN (60 mL), N-bromosuccinimide (4.1 g, 23 mmol) was added portionwise. After stirring at room temperature for 2 h, the reaction mixture was diluted with EtOAc (200 mL), washed with a saturated aq. NaHCO3 (200 mL) and brine (200 mL), then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to afford the sub-title compound as a pale yellow solid (4.0 g, 76%) LCMS calc. for C7H7BrFN2O2 (M+H)+: m/z=249.0. found 249.0.

Workup

  1. washwashed with a saturated aq. NaHCO3 (200 mL) and brine (200 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c3cb830fcd024878afe2dfb899ab2a44
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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