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

HRID 277056

Reaktionsgleichung

Reaktionsgleichung von HRID 277056
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 226296737-Bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamineAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b9ea05ca0bc7405d99a5acc2a36743a9
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355653B1

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