Trimethylsilyl iodide → HCID 135546072, compound

Participants

Reaction Steps

10 cm3 of trimethylsilyl iodide are added to 500 mg of N-[5-bromo-6-[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl]butanamide, prepared previously, and the mixture is refluxed for 4 hours. 25 cm3 of methanol are added and the reaction medium is refluxed for 15 minutes and then concentrated to dryness under reduced pressure (2 kPa; 50° C.). The residue is taken up in 50 cm3 of ethyl acetate and is washed with 2×50 cm3 of 10% sodium thiosulphate solution and then with 50 cm3 of water and 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 then concentrated to dryness under reduced pressure to give 1 g of crude product, which is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3.5 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.) and the residue is taken up in 10 cm3 of ethyl acetate, filtered off, washed with 2×5 cm3 of ethyl acetate and dried (90 Pa; 45° C.) to give 130 mg of N-[5-bromo-6-(4-hydroxyphenyl)-1H-indazol-3-yl]butanamide melting above 260° C.

Provenance & Evidence