Potassium Fluoride → 4-isopropyl-6-methoxy-2-[1-(4-methoxyphenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289841Notes

Reaction equation

HRID 1289841 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([OH:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[N:10]2)=[CH:5][CH:4]=1.Br[CH2:20][N:21]1[C:25](=[O:26])[C:24]2[C:27]([CH:33]([CH3:35])[CH3:34])=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:23]=2[S:22]1(=[O:37])=[O:36].[F-].[K+]>CN(C=O)C.O>[CH:33]([C:27]1[C:24]2[C:25](=[O:26])[N:21]([CH2:20][O:14][C:13]3[N:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[N:10]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:12]=3)[S:22](=[O:37])(=[O:36])[C:23]=2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=1)([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178492075HCID 178492075, compound

Product 1

HCID 189225844-isopropyl-6-methoxy-2-[1-(4-methoxyphenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-(4-methoxyphenyl)-3-trifluoromethyl-5-hydroxy pyrazole (489 mg; 1.89 mmol), 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (600 mg, 1.72 mmol), and KF (200 mg; 3.44 mmol) in DMF (8 ml) was stirred at 20° C. for 2 hours and the mixture was diluted with water. The above mixture was extracted with ether (3×) and the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica gel; 25-50% ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to afford 418 mg (46%) of 4-isopropyl-6-methoxy-2-[1-(4-methoxyphenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =4-CH3O--Ph; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 111°-113° C.

Workup

  1. extractionThe above mixture was extracted with ether (3×)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel; 25-50% ethyl acetate/hexane)
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4f273a3d84504b679202a989a994bee8
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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