Water → 2-(3-cyano-5-methoxyphenoxy)-N-(2-methylpent-3-yn-2-yl)-3-methoxypropionamide

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Reaction Conditions

Reaction Steps

3-Cyano-5-methoxyphenol (prepared as described in J. Med. Chem. (1993), 36, No 16, 2367; 0.119 g) in dry N,N-dimethylformamide (3 ml) containing anhydrous potassium carbonate (0.168 g) and 2-bromo-N-(4-methylpent-2-yn-4-yl) 3-methoxypropionamide (0.210 g) were stirred and heated to 80° C. for 5 hours. The mixture was cooled to ambient temperature, stored for 2 days then poured into water and extracted with ethyl acetate. The organic phases were combined, washed with water, dried over magnesium sulphate then evaporated under reduced pressure to give a brown gum. The gum was fractionated by chromatography (silica; hexane/ethyl acetate 3:2 by volume) to give the required product (0.110 g) as a colourless gum.

Provenance & Evidence