Sodium Carbonate → HCID 51029735, compound

Participants

Reaction Steps

0.072 g (0.23 mmol) of 3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzaldehyde are dissolved in 10 ml of tetrahydrofuran under a stream of nitrogen. The medium is cooled to 0° C. for slow addition of 0.23 ml (0.68 mmol) of a methylmagnesium bromide solution (3M in ethyl ether). The medium is subsequently brought back to ambient temperature and stirred for 1 hour 30 minutes. Neutralization is carried out by adding, under cold conditions and dropwise, a saturated aqueous ammonium chloride solution and then dilution is carried out with dichloromethane and water. The pH of the medium is adjusted to 9-10 by addition of a saturated aqueous sodium carbonate solution. The medium is 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 0.8 g of silica. The residue obtained is purified by chromatography on silica gel, elution of the solid deposit being carried out with a mixture of cyclohexane and ethyl acetate (8/2). 0.056 g (74%) of the expected product is obtained in the form of a white powder.

Provenance & Evidence