Methanol, 1,1-diethoxy-, 1-acetate → 5-Bromo-(1,2,4)triazolo(4,3-a)pyridine

HRID 1945600Notes

Reaction equation

HRID 1945600 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][NH2:9])[CH:5]=[CH:4][CH:3]=1.[C:10](OC(OCC)OCC)(=O)C>CCCCC>[Br:1][C:2]1[N:7]2[CH:10]=[N:9][N:8]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 193925882-Bromo-6-hydrazinopyridine

Product 1

HCID 441183095-Bromo-(1,2,4)triazolo(4,3-a)pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A solution of (6-bromopyridin-2-yl)hydrazine (500 mg, 2.66 mmol) in diethoxymethyl acetate (2.5 mL) was stirred at room temperature for 18 hours. The reaction mixture was diluted with pentane and filtered. The precipitate was washed with pentane and dried at 50° C. under vacuum for 1 hour to give 5-bromo-[1,2,4]triazolo[4,3-a]pyridine as a beige solid (410 mg, 78%). 1H NMR (400 MHz, CHCl3-d): δ 8.98 (s, 1 H); 7.83 (dt, J=9.2, 0.9 Hz, 1 H); 7.22 (dd, J=9.2, 7.0 Hz, 1 H); 7.09 (dd, J=7.0, 0.9 Hz, 1 H).

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with pentane
  3. customdried at 50° C. under vacuum for 1 hour

Sources & evidence

ORD record
ord-f045edc9168a4d579f5e77feb4960888
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…