Iodine → 4-Methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21076

Reaction equation

HRID 21076 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]([OH:22])[N:6]([C:13]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[C:7]2=[O:12].CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.[I:42]I>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([I:42])=[C:8]2[C:4]=1[CH:5]([OH:22])[N:6]([C:13]([CH3:14])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:21])[C:7]2=[O:12]

Participants

6

Reactant 4

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684886364-Methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinoneHCID 178444656HCID 178444656, compound

Product 1

HCID 684911734-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-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (3.55 g, 11.9 mmol) was dissolved in THF (140 mL), and the solution was treated with TMEDA (4.00 mL, 26.2 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 26.4 mL, 26.2 mmol) and iodine (3.62 g, 14.3 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=9/1, 7/3) to obtain 4-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (3.88 g, yield 77%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=9/1, 7/3)

Sources & evidence

ORD record
ord-81f75ec20d134ed9b2b858fa950481b5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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