Reaktion #68650

Reaktionsgleichung

BINAP

sodium tert-butoxide

3-bromo-8-chloro-1,5-naphthyridine

diphenylmethanimine

→

8-chloro-N-(diphenylmethylene)-1,5-naphthyridin-3-amine

Ausbeute 50.0%

Lösungsmittel

toluene

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 25 ml round bottom flask set up under nitrogen
2. 2
   workup.ADDITIONwere added
3. 3
   SonstigeThis was placed in a preheated oil bath at 80° C.
4. 4
   SonstigeReaction
5. 5
   SonstigeFiltrate collected
6. 6
   Einengenwas concentrated
7. 7
   Sonstigeto afford brown oil
8. 8
   SonstigeThis was purified by ISCO silica gel chromatography (40 g, 1% MeOH/DCM over 50 mins)

Vorschrift

A 25 ml round bottom flask set up under nitrogen was charged with Pd2(dba)3 (301 mg, 0.33 mmol), BINAP (614 mg, 0.99 mmol) and sodium tert-butoxide (237 mg, 2.46 mmol). System was purged with Argon and 3-bromo-8-chloro-1,5-naphthyridine (400 mg, 1.64 mmol), diphenylmethanimine (0.28 mL, 1.64 mmol), and toluene (1M, 1.64 mL) were added. This was placed in a preheated oil bath at 80° C. and stirred at this temperature for 16 hours. Reaction cooled to room temperature, diluted with dichloromethane, and passed over a celite cake. Filtrate collected was concentrated to afford brown oil. This was purified by ISCO silica gel chromatography (40 g, 1% MeOH/DCM over 50 mins) to afford clean 8-chloro-N-(diphenylmethylene)-1,5-naphthyridin-3-amine (280 mg, 50% yield). MS[M+H]=344.0. Calc'd for C21H14ClN3=343.8.

Quelle