Potassium Fluoride → HCID 18922583, compound

HRID 1289835Notes

Reaction equation

HRID 1289835 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Br[CH2:16][N:17]1[C:21](=[O:22])[C:20]2[C:23]([CH:29]([CH3:31])[CH3:30])=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:19]=2[S:18]1(=[O:33])=[O:32]>CN(C=O)C>[CH:29]([C:23]1[C:20]2[C:21](=[O:22])[N:17]([CH2:16][O:12][C:11]3[N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=[CH:9][CH:10]=3)[S:18](=[O:33])(=[O:32])[C:19]=2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=1)([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 43511141-phenyl-1H-pyrazol-5(4H)-oneHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 18922583HCID 18922583, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,4-dihydro-2-phenyl-3H-pyrazol-3-one (378 mg; 2.36 mmol) in DMF (6 ml) was added under nitrogen at room temperature 249 mg (4.3 mmol) of KF with stirring followed by 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (750 mg, 2.15 mmol). The resulting mixture was stirred at room temperature for 2 hours and then quenched with saturated ammonium chloride solution. The above mixture was extracted with ether (3×30 ml) and the organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue (yellow solid) was purified by flash chromatography (silica gel; 5% ethyl acetate in methylene chloride) to afford 280 mg (31%) of 4-isopropyl-6-methoxy-2-(1-phenylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =R3 =H; R4 =CH(CH3)2 ; R5 '6-OCH3) as a white solid, m.p. 118°-1190° C.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe above mixture was extracted with ether (3×30 ml)
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue (yellow solid) was purified by flash chromatography (silica gel; 5% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-4c9fb36551a6456fb38cd38839d5a437
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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