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

HRID 1850270Notes

Reaction equation

HRID 1850270 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=1>CC#N>[Br:8][C:12]1[C:13]([NH2:16])=[N:14][CH:15]=[C:10]([F:9])[CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 161264342-Amino-3-bromo-5-fluoropyridineYield 48.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NBS (10 g, 56.2 mmol) was added slowly to a solution of 5-fluoro-pyridin-2-ylamine (55) (12.4 g, 56.2 mmol) in MeCN (200 mL). The reaction mixture was stirred at RT overnight. After completion, the solution was filtered and the filtrate was concentrated to obtain a residue, which was purified by silica gel chromatography (10% to 20% EtOAc in petroleum ether) to give 3-bromo-5-fluoro-pyridin-2-ylamine (56) (5.2 g, 27.2 mmol, 31% yield) as a yellow solid.

Workup

  1. filtrationAfter completion, the solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customto obtain a residue, which
  4. customwas purified by silica gel chromatography (10% to 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-807b54899cbe43579f903a4d5acd56b3
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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