تفاعل #81055

معادلة التفاعل

4-Bromo-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine

vinyltributyltin

→

4-ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine

المردود 42.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was then cooled
2. 2
   أخرىpartitioned between aqueous KF and ethyl acetate
3. 3
   استخلاصThe KF solution was extracted with additional ethyl acetate
4. 4
   غسيلThe organic layers were washed with brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   ترشيحfiltered through silica gel
7. 7
   أخرىevaporated in vacuo
8. 8
   أخرىThe crude oil was then chromatographed on a Prep-500

الإجراء التجريبي

4-Bromo-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (1.0 g, 0.003 mole, Compound No. 57), vinyltributyltin (1.1 g, 0.0034 mole) and trans-benzyl(chloro)bis-(triphenylphosphine)-palladium(II) (20 mg) were heated to 110° C. in DMF (50 mL) under N2 for 4 h. The reaction was then cooled and partitioned between aqueous KF and ethyl acetate. The KF solution was extracted with additional ethyl acetate. The organic layers were washed with brine, dried (MgSO4), filtered through silica gel and then evaporated in vacuo. The crude oil was then chromatographed on a Prep-500 to give 4-ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (0.35 g, 42% yield, Compound No. 55) as a light brown solid.

المصدر