Trifluoroacetic acid → HCID 89545313, compound

HRID 2203405Notes

Reaction equation

HRID 2203405 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.F[C:10](F)(F)C(O)=O>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[CH2:10])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 706222-Amino-5-bromopyridine

Product 1

HCID 89545313HCID 89545313, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-amino-5-bromopyridine (2.34 g, 13.5 mmol) and p-formaldehyde (3.0 g) in toluene (50 mL) was added trifluoroacetic acid (0.1 mL) and the reaction mixture was heated at reflux for 16 h, allowed to cool to ambient temperature, filtered through a pad of diatomaceous earth and concentrated in vacuo. The residue was triturated in methanol to afford 5-bromo-N-methylenepyridin-2-amine as a colorless solid in 34% yield (0.849 g): 1H NMR (300 MHz, CDCl3) δ8.13 (s, 1H), 7.48 (dd, J=8.9, 2.4 Hz, 1H), 6.86 (d, J=8.9 Hz, 1H), 5.51 (s, 2H); MS (ES+) m/z 184.9 (M+1), 186.9 (M+1).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered through a pad of diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in methanol

Sources & evidence

ORD record
ord-684602400aad4f30b6ae96741c8edf63
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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