Acetic Anhydride → 6-Bromo-3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridine

HRID 873993Notes

Reaction equation

HRID 873993 reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].[Br:8][C:9]1[CH:10]=[C:11]([CH3:17])[C:12]([NH:15][NH2:16])=[N:13][CH:14]=1>C1COCC1.O1CCOCC1.C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH3:17])[C:12]2[N:13]([C:1]([CH3:2])=[N:16][N:15]=2)[CH:14]=1

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 534029825-Bromo-2-hydrazinyl-3-methylpyridine

Product 1

HCID 837915436-Bromo-3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridineYield 96.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of acetic anhydride (12.22 mL, 129 mmol) in THF (10 mL) was added over a 10 min period to a suspension of 5-bromo-2-hydrazinyl-3-methylpyridine (25 g, 118 mmol) (Step 130.5) in dioxane (125 mL) and acetic acid (25 mL), at rt. The reaction mixture was stirred for 10 min at rt, heated to 100° C., stirred for 7 h at this temperature, and concentrated. The solid residue was purified by trituration with TBME to provide the title compound (25.7 g) as a colorless solid. tR: 0.39 min (LC-MS 2); ESI-MS: 225.9 [M+H]+ (LC-MS 2).

Workup

  1. temperatureheated to 100° C.
  2. stirringstirred for 7 h at this temperature
  3. concentrationconcentrated
  4. customThe solid residue was purified by trituration with TBME

Sources & evidence

ORD record
ord-760f16ae51164fa6a9668cebcad1bf58
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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