Sodium Iodide → HCID 22171013, compound

HRID 2376204Notes

Reaction equation

HRID 2376204 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22]OS(C)(=O)=O)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Na+].[I-:29]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][I:29])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 23568903HCID 23568903, compound

Product 1

HCID 22171013HCID 22171013, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of methanesulfonic acid 5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-ylmethyl ester (8.80 g, 0.0206 mol) and NaI (4.64 g, 0.0309 mol) in acetone (175 mL) was refluxed for 90 min. The thick reaction slurry was cooled to rt, quenched with H2O (200 mL) and extracted with EtOAc (3×75 mL). The organic layer was dried with Na2SO4, filtered and concentrated to a dark oil. The crude oil was purified by column chromatography (silica gel, 85:15 hexane/EtOAc) to obtain 9.15 g (97%) of the title compound after two steps. HPLC: Rt=11.03 (Method E). MS (ES+): mass calculated for C17H13Cl2IN2O, 459.10; m/z found 460.9 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.37 (d, J=2.0 Hz, 1H), 7.34 (d, J=8.3 Hz, 1H), 7.18 (d, J=8.8 Hz, 2H), 6.95 (dd, J=6.3, 2.0 Hz, 1H), 6.88 (d, J=9.1 Hz, 2H), 6.55 (s, 1H), 4.47 (s, 2H), 3.83 (s, 3H).

Workup

  1. customquenched with H2O (200 mL)
  2. extractionextracted with EtOAc (3×75 mL)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a dark oil
  6. customThe crude oil was purified by column chromatography (silica gel, 85:15 hexane/EtOAc)

Sources & evidence

ORD record
ord-e0778a8402c9420b82131efcf9c02412
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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