Trimethylsilyl iodide → N-(6-(2-chloro-4-hydroxyphenyl)-1H-indazol-3-yl)butyramide

Participants

Reaction Steps

15 cm3 of trimethylsilyl iodide are added to 0.6 g of N-[6-[2-chloro-4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide, described previously, and the mixture is refluxed for 4 hours, followed by addition of 50 cm3 of methanol, and refluxing is continued for 15 minutes. The reaction medium is concentrated to dryness under reduced pressure (2 kPa; 50° C.), 100 cm3 of ethyl acetate are added and the organic phase is washed with 2×50 cm3 of 10% sodium thiosulphate solution and then with 50 cm3 of saturated sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness. The crude product obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); 0.24 g of N-[6-(2-chloro-4-hydroxyphenyl)-1H-indazol-3-yl]butanamide is obtained in the form of a white foam.

Provenance & Evidence