2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide → HCID 131720640, compound

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Reaction Steps

To a mixture 1-(5-chloro-3-trifluoromethyl-2-pyridyl)-3-trifluoromethyl-5-hydroxypyrazole (440 mg; 1.30 mmol) in 8 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 (400 mg, 1.14 mmol) and the resulting mixture was stirred at room temperature for one hour. The mixture was quenched with cold saturated ammonium chloride solution, diluted with water, and extracted with ether (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue (an oil) was purified by flash chromatography (silica gel; 20% ethyl acetate in hexane) and recrystallized from ether/hexane to afford 343 mg (50%) of 4-isopropyyl-6-methoxy-2-[1-(5-chloro-3-trifluoromethyl-2-pyridyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =3-CF3 -5-Cl-2-pyridyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 141°-142° C.

Provenance & Evidence