1,10-Phenanthroline hydrate → 7-Bromo-2-phenyl-[1,2,4]triazolo[1,5-A]pyridine

HRID 517644

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.O.N1[C:23]2[C:14](=[CH:15][CH:16]=[C:17]3[C:22]=2N=CC=C3)[CH:13]=CC=1.O=O.[N:26]#N>[Cu]Br.C(#N)C1C=CC=CC=1>[Br:8][C:6]1[CH:5]=[CH:4][N:3]2[N:26]=[C:13]([C:14]3[CH:23]=[CH:22][CH:17]=[CH:16][CH:15]=3)[N:1]=[C:2]2[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A mixture of 2-amino-4-bromopyridine (5.00 g, 28.3 mmol), copper (I) bromide (207 mg, 1.44 mmol), 1,10-phenanthroline monohydrate (284 mg, 1.44 mmol) and benzonitrile (60 mL) was heated in a 380-mL autoclave to 130° C. and stirred for 23 h under 60 bar of O2/N2 (5:95). After the autoclave was vented and opened (100% conversion, GC method see below), the dark brown reaction suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (40 mL) and dried to yield crude 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (5.71 g, 74%) as a green solid with 100% purity (GC area-%, GC method: column J&W 113-5432 SE-54 (30 m, ID 0.32 mm), oven 80° C. to 140° C. (5° C./min plus 5 min hold) then to 280° C. (10° C./min & 5 min hold), injector 250° C., detector 300° C., carrier gas H2 (66 kPa), split ratio 1/20. Sample preparation: 1-1.5 mg of the sample were dissolved in 1 ml methanol, 2 μl were injected. Retention times: 10.4 min (2-amino-4-bromopyridine), 12.1 min (benzamide), 26.9 (3,5-diphenyl-1,2,4-oxadiazol), 29.8 min (7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine)).

Aufarbeitung

temperaturethe dark brown reaction suspension was then cooled to 0-5° C.
filtrationfiltered
washThe filter cake was washed with TBME (40 mL)
customdried

Quellen und Nachweise

ORD-Eintrag: ord-325aacab220f48ec82e2b2395be65e43
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115130B2

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