Methanol, 1,1-diethoxy-, 1-acetate → 5-Bromo-(1,2,4)triazolo(4,3-a)pyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- filtrationfiltered
- washThe precipitate was washed with pentane
- 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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