Sodium Iodide → HCID 22171013, compound

HRID 1823240Notes

Reaction equation

HRID 1823240 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-ea55281a710d411e8eea4e86726cc282
Source dataset
uspto-grants-2006_05
Patent number
US07037931B2

Reaction notes

Loading…