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Potassium Fluoride → 4-isopropyl-6-methoxy-2-[1-(5-chloro-2-pyridyl)-3-(trifluoromethyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289857
Notes
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Reaction equation

HRID 1289857 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][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.[F-].[K+].Br[CH2:21][N:22]1[C:26](=[O:27])[C:25]2[C:28]([CH:34]([CH3:36])[CH3:35])=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:24]=2[S:23]1(=[O:38])=[O:37]>CN(C=O)C>[CH:34]([C:28]1[C:25]2[C:26](=[O:27])[N:22]([CH2:21][O:13][C:12]3[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=4)[N:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=3)[S:23](=[O:38])(=[O:37])[C:24]=2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=1)([CH3:36])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178516155HCID 178516155, compound

Product 1

HCID 189225504-isopropyl-6-methoxy-2-[1-(5-chloro-2-pyridyl)-3-(trifluoromethyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 1-(5-chloro-2-pyridyl)-3-trifluoromethyl-5-hydroxypyrazole (527 mg; 2 mmol) and KF (232 mg; 4 mmol) in 4 ml of DMF was stirred under nitrogen at room temperature for 20 minutes and then 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (609 mg, 1.75 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour, filtered, and the solid residue was washed with water. The white solid was dissolved in methylene chloride, dried over magnesium sulfate, partially concentrated in vacuo, and the resulting residue was crystallized from ethyl acetate. The combined solid was dried in vacuo to afford 736 mg (79%) of 4-isopropyl-6-methoxy-2-[1-(5-chloro-2-pyridyl)-3-(trifluoromethyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =5-chloro-2-pyridyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 173°-174° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. filtrationfiltered
  3. washthe solid residue was washed with water
  4. dissolutionThe white solid was dissolved in methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationpartially concentrated in vacuo
  7. customthe resulting residue was crystallized from ethyl acetate
  8. customThe combined solid was dried in vacuo

Sources & evidence

ORD record
ord-f5de005e6e9e486d9c117ab2e6b373c2
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05750550

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes