Reaktion #331827

Reaktionsgleichung

6-bromo-4-nitro-1H-indazole

1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate

acetonitrile

→

title compound

Ausbeute 49.7%

6-Bromo-3-fluoro-4-nitro-1H-indazole 6-bromo-4-nitro-1H-indazole

Ausbeute 49.7%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel was sealed
2. 2
   Sonstigeat 150° C.
3. 3
   Sonstigefor two periods of 30 min
4. 4
   SonstigeThe solution was evaporated to dryness
5. 5
   workup.DISSOLUTIONdissolved in chloroform (˜10 ml)
6. 6
   Waschenwas eluted on the Flashmaster 2 with a gradient of 0 to 100% ethyl acetate in cyclohexane over 60 min

Vorschrift

A microwave vial was charged with 6-bromo-4-nitro-1H-indazole (available from Sinova) (363 mg) and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (691 mg) followed by acetonitrile (5 ml) and acetic acid (1 ml). The reaction vessel was sealed and heated under microwave irradiation at 100° C. for two periods of 30 min then at 150° C. for two periods of 30 min. The solution was evaporated to dryness, dissolved in chloroform (˜10 ml) and loaded onto a 20 g silica cartridge which was eluted on the Flashmaster 2 with a gradient of 0 to 100% ethyl acetate in cyclohexane over 60 min. The appropriate fractions were combined and blown to dryness to give the title compound (187 mg) as a yellow solid.

Quelle