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

HRID 1043770Notes

Reaction equation

HRID 1043770 reaction equation
C1C(=O)N([Br:8])C(=O)C1.Cl.[F:10][C:11]1[C:12]([NH2:17])=[N:13][CH:14]=[CH:15][CH:16]=1>C(#N)C>[Br:8][C:15]1[CH:16]=[C:11]([F:10])[C:12]([NH2:17])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 67545931HCID 67545931, compound

Product 1

HCID 508511302-Amino-5-bromo-3-fluoropyridineYield 157.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Solid NBS (750 mg, 4.2 mmol) was added to a solution of 3-fluoropyridin-2-amine HCl salt (1.66 g, 7.18 mmol) in ACN (30 mL) at RT with stirring. The reaction was shielded from light and stirred under nitrogen. After 1 h, an additional amount of NBS (250 mg, 1.4 mmol) was added to the reaction. After 1 h, the solvent was removed under reduced pressure and the residue purified by silica gel flash chromatography eluting with 70% EtOAc/hexane followed by 100% EtOAc to afford 5-bromo-3-fluoropyridin-2-amine as a yellow-brown solid (1.26 g, 92% yield). LC/MS (m/z): 191.0/193.0 (MH+), Rt 1.18 minutes.

Workup

  1. stirringstirred under nitrogen
  2. waitAfter 1 h
  3. customthe solvent was removed under reduced pressure
  4. customthe residue purified by silica gel flash chromatography
  5. washeluting with 70% EtOAc/hexane

Sources & evidence

ORD record
ord-1d3717f8dc68430092cdc3034aecc9b7
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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