Benzonitrile → HCID 67774145, Verbindung

HRID 517647

Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu]Br>[NH2:8][C:6]1[CH:5]=[CH:4][N:3]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=[C:2]2[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of 2,4-diamino-pyridine (1.26 g, 11.5 mmol), copper (I) bromide (82.8 mg, 0.57 mmol), 1,10-phenanthroline monohydrate (114.0 mg, 0.57 mmol) and benzonitrile (13 mL) was heated in a 50 mL 3-necked flask to 150° C. During 41 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (conversion 42%, HPLC method see below). The reaction mixture was then filtered. The resulting clear brown solution was evaporated to dryness and the crude was product purified by silica gel chromatography (hexane/EtOAc 2:8) to yield 7-amino-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (0.72 g, 29%) as a light yellow solid with 99.0% purity (HPLC area-%, HPLC method: X-Bridge C18 column, 150×4.6 mm; mobile phase, A: water/NCMe (95:5), B: NCMe, C: NBu4HSO4 buffer pH 3-4; flow: 1.5 ml/min; gradient from 90/0/10 (A/B/C) to 5/85/10 (A/B/C) within 6 min, isocratic 5/85/10 (A/B/C) for 4 min. Retention time: 0.95 min (2,4-diamino-pyridine), 4.08 min (7-amino-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine)).

Aufarbeitung

customDuring 41 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (conversion 42%, HPLC method see below)
filtrationThe reaction mixture was then filtered
customThe resulting clear brown solution was evaporated to dryness
custompurified by silica gel chromatography (hexane/EtOAc 2:8)

Quellen und Nachweise

ORD-Eintrag: ord-065e9c5424fd4c06b95d96d4f455d4a3
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115130B2

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