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

HRID 1846784Notes

Reaction equation

HRID 1846784 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 (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 get a residue, which was purified by silica gel chromatography to give the product (5.2 g, 31%) as a yellow solid.

Workup

  1. filtrationAfter completion, the solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customto get a residue, which
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-60628e6c5b7f479bbae04d079d3941ec
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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