반응 #87402

반응 방정식

5-(4-Bromo-2-methoxyphenyl)-3-methylpyridazine

sodium tert-butoxide

benzophenone imine

Sodium carbonate

NaOAc

ammonium

→

title compound

수율 93.0%

3-Methoxy-4-(6-methylpyridazin-4-yl)aniline

수율 93.0%

용매

toluene

반응 조건

후처리

1. 1
   기타The flask was purged with N2 three times
2. 2
   온도cooled down
3. 3
   여과filtered through a pad of diatomaceous earth
4. 4
   세척the filter was washed with MTBE
5. 5
   농축The filtrate was concentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in MeOH (60 mL)
7. 7
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature for 10 minutes
9. 9
   농축concentrated under reduced pressure
10. 10
    세척The organic phase was washed with water, brine
11. 11
    건조dried over sodium sulfate
12. 12
    기타the solvent was removed under reduced pressure
13. 13
    기타The residue was purified by flash chromatography on silica gel
14. 14
    세척eluting with 0% to 1% methanol in ethyl acetate

실험 절차

5-(4-Bromo-2-methoxyphenyl)-3-methylpyridazine (1.72 g, 6.20 mmol), Pd2(dba)3 (57 mg, 0.062 mmol), BINAP (116 mg, 0.19 mmol), sodium tert-butoxide (833 mg, 8.68 mmol), benzophenone imine (1.25 mL, 7.44 mmol) and toluene (30 mL) were added into a sealed tube. The flask was purged with N2 three times. The reaction was stirred at 80° C. overnight and then cooled down, filtered through a pad of diatomaceous earth and the filter was washed with MTBE. The filtrate was concentrated. The residue was dissolved in MeOH (60 mL). NaOAc (1.22 g, 14.90 mmol) and ammonium hyxroxide hydrochloride (776 mg, 11.2 mmol) was added. The mixture was stirred at room temperature for 1 hour. Sodium carbonate (1.23 g, 11.60 mmol) was added, and the mixture was stirred at room temperature for 10 minutes and then concentrated under reduced pressure. The residue was taken up in dichloromethane. The organic phase was washed with water, brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 0% to 1% methanol in ethyl acetate to afford the title compound 1.24 g (93%) as a solid.

출처