Propyl mercaptan → HCID 59516113, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-1-(4-methoxycarbonyl-benzyl)-1H-pyrazole-4-carboxylic acid tert-butyl ester (Intermediate #48) (397 mg, 1.13 mmol) was dissolved in butyronitrile (8 mL), potassium carbonate (470 mg, 3.40 mmol) and propanethiol (128 μl, 1.41 mmol) were added and the mixture heated to reflux and stirred at this temperature over night. The reaction mixture was transferred to a microwave vial (using ˜5 ml extra Butyronitrile to ensure complete transfer), a further 3 eq of propane thiol was added and the reaction was heated at 180° C. for 4 hours. EtOAc (˜50 mL) was added and the mixture washed with water (3ט20 mL) and brine (˜20 ml) then dried (MgSO4), filtered and evaporated to give a yellow oil. Oil purified by column chromatography (12 g Si, eluting with 10 to 50% EtOAc in 1H) to yield the title compound as a yellow oil (274 mg, 62%).

Provenance & Evidence