p-Toluenesulfonic acid → HCID 66720869, compound

Participants

Reaction Conditions

Reaction Steps

Put 600 mg (1.08 mmol) of methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-[2-(diphenylmethylidene)hydrazino]pyridine-2-carboxylate, 378 mg (3.78 mmol) of 2,4-pentanedione, 186 mg (1.08 mmol) of paratoluenesulphonic acid and 5 mL of ethanol in a screw-top bottle. Heat the mixture at 120° C. while stirring for 48 h, then cool, and concentrate under reduced pressure. Then distribute the residue in 50 mL of EtOAc and 50 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a heptane/EtOAc gradient from 0 to 50% of EtOAc. After concentration under reduced pressure, we obtain 235 mg of ethyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine-2-carboxylate in the form of oil.

Provenance & Evidence