Sodium Iodide → HCID 22171013, compound

HRID 2376256Notes

Reaction equation

HRID 2376256 reaction equation
[I-:1].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=[C:13]([CH2:24]OS(C)(=O)=O)[CH:12]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]>C1COCC1.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=[C:13]([CH2:24][I:1])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 23568903HCID 23568903, compound

Product 1

HCID 22171013HCID 22171013, compound

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
40 °C

Procedure

Sodium iodide (4.06 kg, 27.1 mol) was added to the THF/toluene solution of methanesulfonic acid 5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-ylmethyl ester (Example 517, 6.32 kg, 14.8 mol). The resulting reaction mixture was heated at 40° C. for 6 h and then allowed to cool to rt overnight. When HPLC analysis indicated the disappearance of the starting material, the reaction was quenched with 28% aq. sodium thiosulfate (6.3 L). The organic layer was washed with sat. aq. NaHCO3 (6.3 L), brine (6.3 L), then dried (MgSO4). After filtration to remove the drying agent, the desired product was obtained in a solution, which was used in the next synthetic step without isolation. Chemical characterization data obtained herein for the title compound is not duplicated in this Example in light of the same data given in Example 1, Step E.

Workup

  1. customThe resulting reaction mixture
  2. temperatureto cool to rt overnight
  3. customthe reaction was quenched with 28% aq. sodium thiosulfate (6.3 L)
  4. washThe organic layer was washed with sat. aq. NaHCO3 (6.3 L), brine (6.3 L)
  5. dry with materialdried (MgSO4)
  6. filtrationAfter filtration
  7. customto remove the drying agent

Sources & evidence

ORD record
ord-68820c302e3948b4be2e3f3d4b0c825f
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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