Potassium Fluoride → HCID 18922547, compound

HRID 1289854Notes

Reaction equation

HRID 1289854 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[C:15]([OH:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[N:12]1.[F-].[K+].Br[CH2:24][N:25]1[C:29](=[O:30])[C:28]2[C:31]([CH:37]([CH3:39])[CH3:38])=[CH:32][C:33]([O:35][CH3:36])=[CH:34][C:27]=2[S:26]1(=[O:41])=[O:40]>CN(C=O)C>[CH:37]([C:31]1[C:28]2[C:29](=[O:30])[N:25]([CH2:24][O:16][C:15]3[N:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[N:12]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:14]=3)[S:26](=[O:41])(=[O:40])[C:27]=2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178516150HCID 178516150, compound

Product 1

HCID 18922547HCID 18922547, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-quinolinyl)-3-trifluoromethyl-5-hydroxypyrazole (533 mg; 1.91 mmol) and KF (220 mg; 3.8 mmol) in 35 ml of DMF was stirred under nitrogen at room temperature for 10 minutes and then 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (592 mg, 1.7 mmol) was added. The reaction mixture was stirred at room temperature for 45 minutes and diluted with ice/cold saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (3×) followed by the addition of ether, the organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was triturated with ethyl acetate/ether to yield a white solid, which was crystallized (from hot ethyl acetate/ether followed by methylene chloride/ether) and dried to afford 710 mg (76%) of 4-isopropyl-6-methoxy-2-[1-(2-quinolinyl)-3-(trifluoromethyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =2-quinolinyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 124°-125° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 45 minutes
  2. additiondiluted with ice/cold saturated sodium bicarbonate solution
  3. extractionThe mixture was extracted with ethyl acetate (3×)
  4. additionfollowed by the addition of ether
  5. washthe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ethyl acetate/ether
  9. customto yield a white solid, which
  10. customwas crystallized (from hot ethyl acetate/ether followed by methylene chloride/ether)
  11. customdried

Sources & evidence

ORD record
ord-982336098bfc40619b40faf67ac3b614
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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