p-Toluenesulfonic acid monohydrate → 6-Bromo-3-(1,1-difluoro-2-methoxyethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 2205748Notes

Reaction equation

HRID 2205748 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]([F:16])([F:15])[CH2:12][O:13][CH3:14])=[N:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([F:16])([F:15])[CH2:12][O:13][CH3:14])=[N:9][N:8]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66849873N'-(5-bromopyridin-2-yl)-2,2-difluoro-3-methoxypropanehydrazide

Product 1

HCID 581189566-Bromo-3-(1,1-difluoro-2-methoxyethyl)-[1,2,4]triazolo[4,3-a]pyridine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N′-(5-bromopyridin-2-yl)-2,2-difluoro-3-methoxypropanehydrazide (0.25 g, 0.81 mmol) and p-toluenesulfonic acid monohydrate (0.12 g, 0.65 mmol) in 1,4-dioxane (3.5 mL) were put onto microwave at 160° C. for 80 min. The reaction mixture was diluted with EtOAc and washed sequentially with NaHCO3 aqueous solution and brine. The organic layer was dried over Na2SO4. Evaporation of the solvent and purification by HPLC gave 6-bromo-3-(1,1-difluoro-2-methoxyethyl)[1,2,4]triazolo[4,3-a]pyridine.

Workup

  1. washwashed sequentially with NaHCO3 aqueous solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customEvaporation of the solvent and purification by HPLC

Sources & evidence

ORD record
ord-ee0afeb6903f4b15a3e5c9417befd970
Source dataset
uspto-grants-2016_06
Patent number
US09371329B2

Reaction notes

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