Methanol → HCID 70313621, compound

Participants

Reaction Steps

0.040 g (1.06 mmol) of sodium borohydride is added portionwise to a solution, cooled to approximately 5° C., of 0.135 g (0.37 mmol) of 3-[2-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-5-yl]-2,6-difluorobenzaldehyde in 10 ml of a mixture of methanol and tetrahydrofuran (1/1). The medium is stirred at ambient temperature for 1 hour, then cooled to 5° C. and then hydrolysed by dropwise addition of 10 ml of a saturated aqueous ammonium chloride solution and 10 ml of water. The mixture is concentrated under reduced pressure and the residue obtained is taken up in 50 ml of dichloromethane and 50 ml of water. The medium is subsequently filtered through a hydrophobic cartridge (70 ml liquid/liquid extraction column, Radleys®) and the organic phase is recovered and concentrated under reduced pressure after having added 1 g of silica. The residue is purified by chromatography on silica gel, elution being carried out with a mixture of cyclohexane and ethyl acetate (8/2). 0.065 g (48%) of the expected product is obtained in the form of a white powder.

Provenance & Evidence