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

HRID 1289863Notes

Reaction equation

HRID 1289863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]([F:21])([F:20])[F:19])[C:5]([N:8]2[C:12]([OH:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)=[N:6][CH:7]=1.Br[CH2:23][N:24]1[C:28](=[O:29])[C:27]2[C:30]([CH:36]([CH3:38])[CH3:37])=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:26]=2[S:25]1(=[O:40])=[O:39]>CN(C=O)C>[C:36](=[C:30]1[CH:27]2[C:28](=[O:29])[N:24]([CH2:23][O:13][C:12]3[N:8]([C:5]4[C:4]([C:18]([F:19])([F:21])[F:20])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=4)[N:9]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:11]=3)[S:25](=[O:40])(=[O:39])[C:26]2=[CH:33][C:32]([O:34][CH3:35])=[CH:31]1)([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178516160HCID 178516160, compound

Product 1

HCID 131720640HCID 131720640, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for one hour
  2. customThe mixture was quenched with cold saturated ammonium chloride solution
  3. additiondiluted with water
  4. extractionextracted with ether (3×)
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue (an oil) was purified by flash chromatography (silica gel; 20% ethyl acetate in hexane)
  8. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-10559e8af2124318876c58577bc8c793
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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