Benzaldehyde → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

HRID 277056

Reaction equation

HRID 277056 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:22])(=O)=O.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[K+]>CO>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:22]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:9]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 114353934-Bromo-2,6-diaminopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 226296737-Bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 96 mg (0.51 mmol) 4-bromo-pyridine-2,6-diamine in 2.4 ml MeOH was added 121 mg (0.56 mmol) O-mesitylenesulfonylhydroxylamine (prepared from ethyl o-mesitylene-sulfonylacetohydroxamate and HClO4 (70%)) in 0.6 ml MeOH at −5° C. and after 15min 71 mg (0.56 mmol) benzaldehyde and stirred for 30 min. The addition of 4.8 ml 1N KOH was followed by extraction with ethylacetate, drying of the organic layer with Na2SO4, and removal of the volatile components. The residue was purified by column chromatography on silica eluting with ethylacetate and hexane (2:3). 58 mg(39%) of 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine were isolated, MS m/e (%): 290 (M++2, 44).

Workup

  1. extractionwas followed by extraction with ethylacetate
  2. dry with materialdrying of the organic layer with Na2SO4, and removal of the volatile components
  3. customThe residue was purified by column chromatography on silica eluting with ethylacetate and hexane (2:3)

Sources & evidence

ORD record
ord-b9ea05ca0bc7405d99a5acc2a36743a9
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Linked notes

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