N-bromobutanimide → 5-Bromo-4-fluoropyridin-2-amine

HRID 1512096Notes

Reaction equation

HRID 1512096 reaction equation
[Br:1]N1C(=O)CCC1=O.OC(C(F)(F)F)=O.[F:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1>C(#N)C>[Br:1][C:22]1[C:17]([F:16])=[CH:18][C:19]([NH2:23])=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866401984-fluoropyridin-2-amine TFA salt

Product 1

HCID 579174075-Bromo-4-fluoropyridin-2-amineYield 67.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (126 mg, 0.71 mmol) was added to a solution of 4-fluoropyridin-2-amine TFA salt (162 mg, 0.72 mmol) in acetonitrile (4 mL) in an aluminum foil-wrapped flask in a darkened hood. The reaction solution was stirred at room temperature in darkness for 2 hours. After evaporation of the solvent, the crude product was purified on a silica gel column eluting with EtOAc to give 5-bromo-4-fluoropyridin-2-amine as an ivory solid (92 mg, 67%). LC/MS (m/z): 190.9/192.9 (MH+), Rt 1.02 minutes.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was purified on a silica gel column
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-8f461e35a79c4180a04f19191e00989a
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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