Iodine → 4-Methoxymethoxy-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21270Notes

Reaction equation

HRID 21270 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]([OH:26])[N:8]([C:17]([CH3:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:9]2=[O:16].CN(CCN(C)C)C.[I:35]I>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([I:35])=[C:10]2[C:6]=1[CH:7]([OH:26])[N:8]([C:17]([CH3:18])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:25])[C:9]2=[O:16]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684927044-Methoxymethoxy-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684898104-Methoxymethoxy-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-methoxymethoxy-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.00 g, 5.60 mmol) was dissolved in THF (60 mL), and the solution was treated with TMEDA (2.70 mL, 17.9 mmol), sec-butyl lithium-hexane solution (0.95 mol/L, 18.9 mL, 18.0 mmol) and iodine (2.13 g, 8.39 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30) to obtain 4-methoxymethoxy-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenyl ethyl)isoindolinone (2.08 g, yield 77%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30)

Sources & evidence

ORD record
ord-72f07bd9f37440849c91c630b11e306b
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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