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

HRID 21085Notes

Reaction equation

HRID 21085 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]([OH:24])[N:8]([C:15]([CH3:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[C:9]2=[O:14].CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.[I:44]I>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([I:44])=[C:10]2[C:6]=1[CH:7]([OH:24])[N:8]([C:15]([CH3:16])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:23])[C:9]2=[O:14]

Participants

6

Reactant 4

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684896664-Methoxymethoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinoneHCID 178444656HCID 178444656, compound

Product 1

HCID 684919774-Methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-methoxymethoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (8.50 mg, 26.0 mmol) was dissolved in THF (340 mL), and the solution was treated with TMEDA (12.5 mL, 83.1 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 8.4.0 mL, 83.1 mmol) and iodine (7.91 g, 31.2 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=90/10, 70/30) to obtain 4-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (7.65 g, yield 65%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=90/10, 70/30)

Sources & evidence

ORD record
ord-3262e99be0504d1b82c58de180014fd5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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