Hydrogen Peroxide → HCID 89987939, compound

HRID 623749Notes

Reaction equation

HRID 623749 reaction equation
[C:1](I)([F:4])([F:3])[F:2].[CH2:6]([N:13]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:14]1[C:26]([OH:28])=[O:27])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.OO>CS(C)=O.O>[CH2:6]([N:13]1[C:17]([C:1]([F:4])([F:3])[F:2])=[C:16]([CH3:18])[C:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:14]1[C:26]([OH:28])=[O:27])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 16843TrifluoroiodomethaneHCID 86711836HCID 86711836, compound

Product 1

HCID 89987939HCID 89987939, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

CF3I (10 g) gas was bubbled through a solution of 1-benzyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrole-2-carboxylic acid (4.0 g, 12.94 mmol) in DMSO (40 mL) and FeSO4.7H2O (2.15 g, 7.76 mmol) at RT for 5 min. 30% Aqueous H2O2 (8.7 mL, 77.64 mmol) was then added at 0° C. and stirring was continued at room temperature for 16 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (1×100 mL) and brine (50 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; 60-120 mesh); it eluted with 10-12% EtOAc in petroleum ether to yield ACI-09 (1.7 g, 35%) as a white solid.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with water (1×100 mL) and brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel; 60-120 mesh)
  6. washit eluted with 10-12% EtOAc in petroleum ether
  7. customto yield ACI-09 (1.7 g, 35%) as a white solid

Sources & evidence

ORD record
ord-c06dc669b7ea4a31aba2af68171f5cee
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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