Acetic Acid → 8-Bromo-3-methyl-[1,2,4]triazolo[4,3-A]pyridine

HRID 1888196Notes

Reaction equation

HRID 1888196 reaction equation
[Br:1][C:2]1[C:3]([NH:8][NH:9][C:10](=O)[CH3:11])=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]2[N:4]([C:10]([CH3:11])=[N:9][N:8]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66924560N'-(3-bromopyridin-2-yl)acetohydrazide

Product 1

HCID 669245028-Bromo-3-methyl-[1,2,4]triazolo[4,3-A]pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 0.17 g (0.74 mmol) of N′-(3-bromopyridin-2-yl)acetohydrazicle from step A in 40 mL of anhydrous toluene was added 3 mL of glacial acetic acid and the resulting mixture was heated to reflux for 20 h employing a Dean-Stark trap. The reaction mixture was cooled to ambient temperature then evaporated to dryness in vacuo to afford the title compound (0.13 g, 84%) LC-MS: m/z (ES) 212, 214 (MH)+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 20 h
  3. customthen evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5cb8e3fce1b64356aeea3efbea764c55
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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