Bromine → 2-Bromo-6-fluoropyridin-3-amine

HRID 2382135Notes

Reaction equation

HRID 2382135 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][N:5]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:6]1[C:7]([NH2:10])=[CH:8][CH:9]=[C:4]([F:3])[N:5]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 573641272-Bromo-6-fluoropyridin-3-amineYield 90.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (1.96 g, 12.2 mmol) is added to a mixture of 2-fluoro-5-aminopyridine (1.37 g, 12.2 mmol) and sodium acetate (2 mg, 24.4 mmol) in acetic acid (30 mL) and stirred at rt for 4 hours. Acetic acid is evaporated off in vacuo. The residue is dissolved in EtOAc (50 mL), washed with saturated aqueous Na2CO3 (10 mL), water (20 mL) and brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo to afford 2-bromo-3-amino-6-fluoropyridine (2.1 g) as a solid. MS: 190 (M+H); 1H NMR (300 MHz, CDCl3): δ 4.04 (br, 2H), 6.77 (dd, H), 7.17(dd, H).

Workup

  1. customAcetic acid is evaporated off in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (50 mL)
  3. washwashed with saturated aqueous Na2CO3 (10 mL), water (20 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4962c61ed715483cb100a2f58454d116
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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