Phosphorus oxychloride → HCID 59233259, Verbindung
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]([C:14]2[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)([F:13])[F:12])=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([C:14]3[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([F:13])[F:12])=[N:9][N:8]=2)[CH:7]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
A mixture of N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide (1.0 g, 2.64 mmol) and PCl5 (1.2 g, 8 mmol) in POCl3 (40.5 g, 264 mmol) was heated at 140° C. in a sealed tube for 18 hrs. Solvent was removed via rotary evaporation, and the resulting residue was reconstituted in EtOAc. The organic solution was washed with saturated NaHCO3, dried with MgSO4, filtered, and concentrated to dryness. The resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient) to provide the title compound, 6-bromo-3-((6-chloropyridazin-3-yl)difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine 45F (0.8 g, 2.21 mmol, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (dd, J=9.85, 1.77 Hz, 1 H) 8.01 (dd, J=9.85, 1.01 Hz, 1 H) 8.31 (d, J=9.09 Hz, 1 H) 8.42-8.51 (m, 1 H) 8.93 (s, 1 H). ESI-MS:m/z 359.9 (M+H)+.
Aufarbeitung
- customSolvent was removed via rotary evaporation
- washThe organic solution was washed with saturated NaHCO3
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-1b360e952c4746729feba85fba6764cc
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08178534B2
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