Nitrogen → 6-Bromo-5-fluoropyridin-3-amine

HRID 1044796Notes

Reaction equation

HRID 1044796 reaction equation
N#N.[NH2:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([F:10])[CH:9]=1.[Br:11]N1C(=O)CCC1=O>CN(C=O)C>[NH2:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([Br:11])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 67184N-bromobutanimideHCID 5744505-Fluoro-3-pyridinamine

Product 1

HCID 717413826-Bromo-5-fluoropyridin-3-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 3-amino-5-fluoropyridine (900 mg, 8.03 mmol) in dry DMF (13 mL) was treated at 0° C. with N-bromo-succinimide (1.43 g, 8.03 mmol). The reaction mixture was stirred at rt until completion of the reaction. The mixture was then partitioned between Et2O and water. The layers were separated and the org. layer successively washed with water, sat. aq. NaHCO3 and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA 9:1 to 1:1) and the title compound obtained as an orange solid. LC-MS-conditions 07: tR=0.52 min; [M+H]+=191.30.

Workup

  1. customThe mixture was then partitioned between Et2O and water
  2. customThe layers were separated
  3. washlayer successively washed with water, sat. aq. NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by FC (hept-EA 9:1 to 1:1)

Sources & evidence

ORD record
ord-39b1c6ab9b8546eeb0c811a4edf087e7
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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