Methanol, 1,1-diethoxy-, 1-acetate → 6-Fluoro-[1,2,4]triazolo[4,3-a]pyridine

HRID 2282396Notes

Reaction equation

HRID 2282396 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10](OC(OCC)OCC)(=O)C>C1CCCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[N:9][N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 552672456-Fluoro-[1,2,4]triazolo[4,3-a]pyridineYield 70%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

(5-Fluoro-pyridin-2-yl)-hydrazine (500 mg, 3.93 mmol) in diethoxymethyl acetate (5 mL) was stirred at RT for 2 h. The resulting precipitate was diluted with cyclohexane (5 ml) and filtered to give the title compound (379 mg, 70%). 1H NMR (400 MHz, CDCl3): 7.25 (1H, m), 7.84 (1H, m), 8.09 (1H, t), 8.84 (1H, s).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-acca879eb57d4ccc9040f7ea3f5e3016
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

Loading…