تفاعل #979964

معادلة التفاعل

hydrochloric acid

isopropyl magnesium chloride

Ethyl potassium malonate

6-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-3-oyl chloride

sodium bicarbonate

→

title compound

المردود 63.0%

Ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate

المردود 63.0%

المذيبات

tetrahydrofuran

THF

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe suspension was sonicated for 1/2 hour
2. 2
   أخرىgiving a homogeneous solution
3. 3
   workup.ADDITIONThis was added
4. 4
   workup.STIRRINGstirred for 15 minutes
5. 5
   استخلاصThe aqueous phase was extracted with dichloromethane (2×10 ml)
6. 6
   تجفيفdried over magnesium sulphate
7. 7
   أخرىthe solvent removed under reduced pressure

الإجراء التجريبي

Ethyl potassium malonate (57 mg) was suspended in dry tetrahydrofuran (1 ml) and 2M isopropyl magnesium chloride in THF (170 μl) added. The suspension was sonicated for 1/2 hour giving a homogeneous solution. This was added with stirring to the suspension of 6-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-3-oyl chloride in dichloromethane. The mixture was stirred at room temperature for 1/2 hour. It was then poured into 1N hydrochloric acid, stirred for 15 minutes and adjusted to pH8 with saturated sodium bicarbonate. The aqueous phase was extracted with dichloromethane (2×10 ml), the extracts combined, dried over magnesium sulphate and the solvent removed under reduced pressure yielding the title compound as a pale red oil (40 mg, 63%) [as a 1:1 mixture of enol and keto tautomers].

المصدر