Trifluoroacetic acid → 1h-Isoindol-1-one,2,3-dihydro-4-hydroxy-7-iodo-5-(methoxymethyl)-

HRID 21255Notes

Reaction equation

HRID 21255 reaction equation
COC[O:4][C:5]1[C:13]([CH:14](OC)[O:15][CH3:16])=[CH:12][C:11]([I:19])=[C:10]2[C:6]=1[CH:7](O)[N:8](C(C)(C1C=CC=CC=1)C)[C:9]2=[O:20].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[OH:4][C:5]1[C:13]([CH2:14][O:15][CH3:16])=[CH:12][C:11]([I:19])=[C:10]2[C:6]=1[CH2:7][NH:8][C:9]2=[O:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68489206HCID 68489206, compound

Product 1

HCID 684932311h-Isoindol-1-one,2,3-dihydro-4-hydroxy-7-iodo-5-(methoxymethyl)-Yield 86%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-methoxymethoxy-5-dimethoxymethyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (200 mg, 0.379 mmol) was dissolved in nitromethane (10 mL), and the solution was treated with trifluoroacetic acid (0.584 mL, 7.58 mmol) and triethylsilane (0.612 mL, 3.79 mmol), followed y purification by slurry using chloroform to obtain 4-hydroxy-5-methoxymethyl-7-iodoisoindolinone (103 mg, yield-86%).

Workup

  1. customy purification by slurry

Sources & evidence

ORD record
ord-005bd4589835411884785a841adffc41
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

Loading…