2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide → HCID 18922610, compound

HRID 1289865Notes

Reaction equation

HRID 1289865 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[C:7]([N:9]2[C:13]([OH:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[N:10]2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:22][N:23]1[C:27](=[O:28])[C:26]2[C:29]([CH:35]([CH3:37])[CH3:36])=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:25]=2[S:24]1(=[O:39])=[O:38]>CN(C=O)C>[CH:35]([C:29]1[C:26]2[C:27](=[O:28])[N:23]([CH2:22][O:14][C:13]3[N:9]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[N:8]=4)[N:10]=[C:11]([C:15]([F:17])([F:16])[F:18])[CH:12]=3)[S:24](=[O:39])(=[O:38])[C:25]=2[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=1)([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178516153HCID 178516153, compound

Product 1

HCID 18922610HCID 18922610, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture 1-(6-trifluoromethyl-2-pyridyl)-3-trifluoromethyl-5-hydroxypyrazole (420 mg; 1.41 mmol) in 10 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 (410 mg, 1.17 mmol) and the resulting mixture was stirred at room temperature for one hour, quenched with cold saturated ammonium chloride solution, and extracted with ether (3×). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue (a solid) was purified by flash chromatography (silica gel; 5-20% ethyl acetate in hexane) and recrystallized from ether/hexane to afford 420 mg (63%) of 4-isopropyl-6-methoxy-2-[1-(6-trifluoromethyl-2-pyridyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =6-CF3 -2-pyridyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 149°-150° C.

Workup

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

Sources & evidence

ORD record
ord-223c00d160bb4517913580add03e5783
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

Loading…