Methyl 5-ethynylnicotinate → 3-{6-[2-(5-methoxycarbonyl-3-pyridyl)-ethinyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

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Reaction Steps

Under the conditions of example 5A, 184 mg of the crude 5-ethinylnicotinic acid methyl ester is reacted with 500 mg of 3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate and for complete purification subjected to high-pressure liquid chromatography on reversed-phase silica gel (Nova-Pak HR C18) with acetonitrile/water=75/25. 15 mg of 3-{6-[2-(5-methoxycarbonyl-3-pyridyl)-ethinyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Provenance & Evidence