N-bromobutanimide → 2-Amino-5-bromo-3-fluoropyridine

HRID 2237933Notes

Reaction equation

HRID 2237933 reaction equation
[F:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:16])C(=O)C1.C([O-])(O)=O.[Na+]>C(#N)C>[Br:16][C:6]1[CH:7]=[C:2]([F:1])[C:3]([NH2:8])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 27628092-Amino-3-fluoropyridine

Product 1

HCID 508511302-Amino-5-bromo-3-fluoropyridineYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 3-fluoro-pyridin-2-ylamine (example C.29 step 2) (3 g, 26.8 mmol) in acetonitrile (50 mL) at 0° C. was added NBS (4.77 g, 26.8 mmol) and the mixture was stirred at 23° C. for 2 h. Poured on ice with sat. NaHCO3-sol., extracted thrice with AcOEt, dried over Na2SO4. Removal of the solvent in vacuum left a residue, which was purified by silica gel column chromatography with heptane/AcOEt 3:1 to give the title compound as a brown solid (3.1 g, 60%). MS (ISP) 191 [(M+H)+], 193 [(M+2+H)+].

Workup

  1. customat 0° C.
  2. extraction, extracted thrice with AcOEt
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a residue, which
  6. customwas purified by silica gel column chromatography with heptane/AcOEt 3:1

Sources & evidence

ORD record
ord-6baebd7e62f9445197771f6343f6caae
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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