Reaktion #979964

Reaktionsgleichung

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

Ausbeute 63.0%

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

Ausbeute 63.0%

Lösungsmittel

tetrahydrofuran

THF

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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].

Quelle