Tetrahydrofuran → Methyl 3-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]benzoate

Participants

Reaction Conditions

Reaction Steps

Under a stream of nitrogen, 0.400 g (1.37 mmol) of 5-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine obtained in step 5.3, 0.300 g (1.67 mmol) of 3-methoxycarbonylphenylboronic acid and 1.330 g (4.08 mmol) of caesium carbonate are placed in 5 mL of a 9/1 mixture of tetrahydrofuran and water. 0.11 g (0.13 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) is added and the medium is heated at 70° C. for 4 hours. The medium is then cooled to room temperature and diluted with 40 mL of dichloromethane and 40 mL of water. The medium is then filtered on a hydrophobic cartridge (Radleys® 70 mL liquid/liquid extraction column) and the organic phase is recovered and concentrated under reduced pressure after addition of 2 g of silica. The residue is purified by chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (9/1). 0.340 g (71%) of expected product is obtained in the form of a white powder.

Provenance & Evidence