Iodide Ion → HCID 10427137, compound

Participants

Reaction Steps

4-[2,5-Dimethyl-3-(4-fluorophenyl)-1H-indol-1-yl]-1-methylpyridinium, iodide 8a (3.0 g) was dissolved in acetic acid (75 ml) and PtO2 (0.4 g) was added. After hydrogenation for 2 weeks at 3 ato the catalyst was filtered off, the acetic acid was evaporated in vacuo and water (50 ml) was added. The thus obtained acidic solution was made alkaline (pH>9) with concentrated sodium hydroxide and extracted with ethyl acetate (2×50 ml). The organic phases were successively washed with diluted sodium hydroxide (50 ml), washed with brine and dried (Na2SO4). Evaporation of the solvent gave 1.3 g of the title compound as an oil, which was purified by column chromatography on silica gel (eluted with ethyl acetate/ethanol 8:1 containing 4% triethylamine) and crystallized from heptane. Yield 0.4 g, mp 110°-112° C.

Provenance & Evidence