Trifluoroacetic acid → 4-Hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21094Notes

Reaction equation

HRID 21094 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH:7](O)[N:8]([C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:9]2=[O:15].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[OH:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH2:7][N:8]([C:16]([CH3:24])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:17])[C:9]2=[O:15].[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH2:7][N:8]([C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:9]2=[O:15]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684919774-Methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Product 2

HCID 684893914-Hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 59%HCID 68490938HCID 68490938, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (500 mg, 1.10 mmol) was dissolved in nitromethane (25 mL), and the solution was treated with trifluoroacetic acid (0.525 mL, 6.82 mmol) and triethylsilane (0.527 mL, 3.30 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/0, 99/1) to obtain 4-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (257 mg, yield 59%) and 4-methoxymethoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (131 mg, yield 27%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=100/0, 99/1)

Sources & evidence

ORD record
ord-d928066073f843f3bedb7368cd7aa256
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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