Pyridine → HCID 178477618, compound

Participants

Reaction Conditions

Reaction Steps

305 mg of 2-methyl-3-ethylsulfinyl-4-methylsulfonylbenzoic acid and 106 mg of 3-hydroxy-2-methylpyrazole are suspended in 2 ml of ethyl acetate and 407 mg of pyridine under an inert atmosphere and cooled to −25° C. with stirring. 129 mg of thionyl chloride are then slowly added dropwise such that the temperature always remains below −20° C. Following the complete addition of the thionyl chloride, the mixture is stirred for a further 20 minutes. A further 27 mg of 3-hydroxy-2-methylpyrazole are added, and 42 mg of thionyl chloride are slowly added dropwise such that the temperature always remains below −25° C. 4 μl of cold water are then added and the mixture is warmed to 0° C. After separating the organic phase from the aqueous phase, the aqueous phase is extracted twice with 5 ml of ethyl acetate in each case. The combined organic phases are dried, giving 370 mg of [3-(ethylsulfinyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone (91% yield).

Provenance & Evidence