Water → HCID 68490869, compound

HRID 21249Notes

Reaction equation

HRID 21249 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH:4](O)[N:5](C(C)(C1C=CC=CC=1)C)[C:6]2=[O:13].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>[N+](C)([O-])=O.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]

Participants

8

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68492849HCID 68492849, compound

Product 1

HCID 68490869HCID 68490869, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 6375NitromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-chloro-5-methyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (300 mg, 0.679 mmol) was dissolved in nitromethane (5 mL), and the solution was added with trifluoroacetic acid (0.523 mL, 6.79 mmol) and triethylsilane (0.219 mL, 1.36 mmol), followed by stirring at room temperature for 24 hours. The reaction mixture was added with water, ethyl acetate and hexane. The precipitated solid was collected by filtration and washed with hexane and water, followed by drying under reduced pressure to obtain 4-chloro-5-methyl-7-iodoisoindolinone (140 mg, yield 67%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with hexane and water
  3. customby drying under reduced pressure

Sources & evidence

ORD record
ord-399814e10a9d452698360da1f9f925ee
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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