Reaction #1528430

Reaction equation

4-bromo-6-methoxy-[1,5]naphthyridin-3-ylamine

nitrosonium tetrafluoroborate

→

title compound

Yield 90.0%

4-Bromo-6-methoxy-[1,5]naphthyridine-3-diazonium tetrafluoroborate

Yield 90.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added portionwise over 30 min (approximately 2 g portions)
2. 2
   FiltrationThe orange solid was collected by suction filtration
3. 3
   Washwashed with ice-cold THF
4. 4
   Otherdried under vacuum

Procedure

A solution of 4-bromo-6-methoxy-[1,5]naphthyridin-3-ylamine (25.2 g, 99.2 mmole) in dry THF (400 mL) was maintained at −5° C. while nitrosonium tetrafluoroborate (12.9 g, 110 mmole) was added portionwise over 30 min (approximately 2 g portions). The reaction was continued for an additional 1 hr at −5° C., at which time TLC* and LC/MS indicated that the reaction was complete. The orange solid was collected by suction filtration, washed with ice-cold THF and dried under vacuum to provide the title compound (31.42 g, 90%).

Source