Chloride → HCID 13849599, compound

Participants

Reaction Steps

Propyne (3.0 mLs, 0.045 mol) is condensed in a graduated cylinder in a dry ice/acetone bath and added to a stirred suspension of dimethyl 1,6-dihydro-5-iodo-6-oxo-2,3-pyridinedicarboxylate (13.48 g, 0.04 mol), cuprous iodide (0.38 g, 0.002 mol) and bis(triphenylphosphine)palladium II) chloride (2.81 g, 0.004 mol) in 150 mLs DMSO and 50 mLs triethylamine at 10° C. After addition of the propyne the reaction mixture is stirred at room temperature for 60 hours. Water is added and the mixture is extracted with ethyl acetate. The ethyl acetate solution is washed with water and dried over anhydrous MgSO4, then concentrated in vacuo to give a mixture of materials. The crude product is isolated by flash column chromatography using 9:1 methylene chloride:ethyl acetate. The fractions containing the title product are concentrated in vacuo and the residue is recrystallized from cyclohexane to give the pure compound mp 115°-118° C.

Provenance & Evidence