Sodium Iodide → HCID 9949709, compound

Participants

Reaction Steps

Prepared as in Example 48, via the following four-step sequence: 2-(2,5-dimethylpyrrolyl)-6-[4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl]-pyridine was first alkylated with 2-chlorocyclohexanone, using potassium carbonate as the base and a catalytic amount of sodium iodide, in dimethylformamide at 80° C. for 24 hours, in 92% yield. The resulting ketone was converted to the oxime methyl ether using O-methylhydroxylamine hydrochloride and triethylamine in methanol at reflux for 16 h in 81% yield. The oxime ether was then reduced to the amine using borane methyl sulfide in tetrahydrofuran at reflux for 2 days, followed by refluxing in ethanol with sodium carbonate and cesium fluoride for 16 hours, in 12% yield. The amine was then deblocked with hydroxylamine hydrochloride in refluxing aqueous ethanol to afford the desired final product in 89% yield as a tan solid after conversion to the hydrochloride salt.

Provenance & Evidence