2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide → HCID 18922610, compound

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Reaction Steps

To a mixture 1-(6-trifluoromethyl-2-pyridyl)-3-trifluoromethyl-5-hydroxypyrazole (420 mg; 1.41 mmol) in 10 ml of DMF was added under nitrogen KF (132 mg, 2.28 mmol) and the mixture was stirred at room temperature for 10 minutes. To the above mixture was added 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (410 mg, 1.17 mmol) and the resulting mixture was stirred at room temperature for one hour, quenched with cold saturated ammonium chloride solution, and extracted with ether (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue (a solid) was purified by flash chromatography (silica gel; 5-20% ethyl acetate in hexane) and recrystallized from ether/hexane to afford 420 mg (63%) of 4-isopropyl-6-methoxy-2-[1-(6-trifluoromethyl-2-pyridyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =6-CF3 -2-pyridyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 149°-150° C.

Provenance & Evidence