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

HRID 1922750Notes

Reaction equation

HRID 1922750 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-7d842cdc7bc74c5e807be88058782bde
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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