Tetrabutylammonium Fluoride → HCID 10380885, compound

Participants

Reaction Steps

2.9 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 900 mg of N-[6-(2-chlorophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 40 cm3 of tetrahydrofuran, and the mixture is refluxed for 18 hours. The reaction medium is diluted with 50 cm3 of ethyl acetate and the organic phase is washed successively with 2×30 cm3 of saturated sodium hydrogen carbonate solution, with 30 cm3 of water and with 30 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 (2 kPa; 50° C.). 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 (90/10 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); 120 mg of N-[6-(2-chlorophenyl)-1H-indazol-3-yl]butanamide are obtained in the form of a beige-coloured foam.

Provenance & Evidence