4-Bromo-6-methoxy-[1,5]naphthyridine-3-diazonium tetrafluoroborate → 8-Bromo-7-fluoro-2-methoxy-1,5-naphthyridine

HRID 638986

Reaktionsgleichung

[F:1][B-](F)(F)F.[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[N:15]=2)[N:10]=[CH:9][C:8]=1[N+]#N>C1C2C(CCCC2)CCC1.C(Cl)(Cl)Cl>[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[N:15]=2)[N:10]=[CH:9][C:8]=1[F:1]

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

A suspension of 4-bromo-6-methoxy-[1,5]naphthyridine-3-diazonium tetrafluoroborate (31.42 g, 89.0 mmol) in decalin (mixed isomers, 500 mL) in a 2 L flask* was heated to 180° C. and held at this temperature for 5 min. The mixture was cooled and diluted with CHCl3 (500 mL, to keep the product in solution), and the resulting mixture was stirred vigorously for 30 min to break up a black solid byproduct. The mixture was then poured onto a column of silica gel and the column was eluted with CHCl3 to remove decalin and then with 3% EtOAc/CHCl3 to afford the title compound (9.16 g, 40%).

Aufarbeitung

temperatureThe mixture was cooled
additionThe mixture was then poured onto a column of silica gel
washthe column was eluted with CHCl3
customto remove decalin

Quellen und Nachweise

ORD-Eintrag: ord-d8ced98fc8c34c459e21c97cff70057e
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07691850B2

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