反応 #68650

反応方程式

BINAP

sodium tert-butoxide

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

diphenylmethanimine

→

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

収率 50.0%

溶媒

toluene

dichloromethane

反応条件

後処理

1. 1
   その他A 25 ml round bottom flask set up under nitrogen
2. 2
   workup.ADDITIONwere added
3. 3
   その他This was placed in a preheated oil bath at 80° C.
4. 4
   その他Reaction
5. 5
   その他Filtrate collected
6. 6
   濃縮was concentrated
7. 7
   その他to afford brown oil
8. 8
   その他This was purified by ISCO silica gel chromatography (40 g, 1% MeOH/DCM over 50 mins)

実験手順

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.

出典