تفاعل #87402

معادلة التفاعل

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

sodium tert-butoxide

benzophenone imine

Sodium carbonate

NaOAc

ammonium

→

title compound

المردود 93.0%

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

المردود 93.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىThe flask was purged with N2 three times
2. 2
   درجة الحرارةcooled down
3. 3
   ترشيحfiltered through a pad of diatomaceous earth
4. 4
   غسيلthe filter was washed with MTBE
5. 5
   تركيزThe 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
   تركيزconcentrated under reduced pressure
10. 10
    غسيلThe organic phase was washed with water, brine
11. 11
    تجفيفdried over sodium sulfate
12. 12
    أخرىthe solvent was removed under reduced pressure
13. 13
    أخرىThe residue was purified by flash chromatography on silica gel
14. 14
    غسيلeluting with 0% to 1% methanol in ethyl acetate

الإجراء التجريبي

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.

المصدر