N-bromobutanimide → 2-Amino-5-bromopyridine-4-carbonitrile

HRID 1512097Notes

Reaction equation

HRID 1512097 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][N:16]=1)[C:12]#[N:13].[Br:17]N1C(=O)CCC1=O>C(#N)C>[NH2:8][C:9]1[CH:10]=[C:11]([C:14]([Br:17])=[CH:15][N:16]=1)[C:12]#[N:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 866458862-amino-isonicotinonitrile TFA salt

Product 1

HCID 534405772-Amino-5-bromopyridine-4-carbonitrileYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In an aluminum foil-covered flask in a darkened hood, 2-amino-isonicotinonitrile TFA salt (125 mg, 0.54 mmol) was dissolved in acetonitrile (3.5 mL). Solid N-bromosuccinimide (89.2 mg, 0.501 mmol) was added to the stirred solution in one portion at RT. The reaction solution was stirred at room temperature in darkness for 90 minutes. After evaporation of the solvent, the crude material was further purified by silica gel chromatography to give 2-amino-5-bromo-isonicotinonitrile (53 mg, 49%). LC/MS (m/z): 197.9 (MH+), Rt 2.92 minutes.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude material was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-c533a0072a9d484096fe2201b4164505
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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