Trifluoroacetic acid → 4-Hydroxy-5-methoxy-7-iodoisoindolinone

HRID 21271Notes

Reaction equation

HRID 21271 reaction equation
COC[O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([I:16])=[C:10]2[C:6]=1[CH:7](O)[N:8](C(C)(C1C=CC=CC=1)C)[C:9]2=[O:17].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[OH:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([I:16])=[C:10]2[C:6]=1[CH2:7][NH:8][C:9]2=[O:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684898104-Methoxymethoxy-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684899574-Hydroxy-5-methoxy-7-iodoisoindolinoneYield 71%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-methoxymethoxy-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (763 mg, 1.58 mmol) was dissolved in nitromethane (12 mL), and the solution was treated with trifluoroacetic acid (1.22 mL, 15.8 mmol) and triethylsilane (2.55 mL, 15.8 mmol), followed by purification by slurry using chloroform to obtain 4-hydroxy-5-methoxy-7-iodoisoindolinone (341 mg, yield 71%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-dca9ec98d00040359a79974573c43175
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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