Trifluoroacetic acid → HCID 68491952, compound

HRID 21073Notes

Reaction equation

HRID 21073 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]2[C:3]=1[CH:4](O)[N:5](C(C)(C1C=CC=CC=1)C)[C:6]2=[O:12].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684917904-Fluoro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 68491952HCID 68491952, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-fluoro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (1.17 g, 2.86 mmol) was dissolved in nitromethane (46 mL), and the solution was treated with trifluoroacetic acid (2.20 mL, 28.6 mmol) and triethylsilane (0.914 mL, 5.72 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/0, 85/15) to obtain 4-fluoro-7-iodoisoindolinone (586 mg, yield 74%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=100/0, 85/15)

Sources & evidence

ORD record
ord-ba7660f0e0684e9b96b1c205011166f2
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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