Iodine → HCID 68489206, compound

HRID 21254Notes

Reaction equation

HRID 21254 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([CH:14]([O:17][CH3:18])[O:15][CH3:16])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]([OH:29])[N:8]([C:20]([CH3:28])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21])[C:9]2=[O:19].CN(CCN(C)C)C.[I:38]I>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([CH:14]([O:15][CH3:16])[O:17][CH3:18])=[CH:12][C:11]([I:38])=[C:10]2[C:6]=1[CH:7]([OH:29])[N:8]([C:20]([CH3:21])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH3:28])[C:9]2=[O:19]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 68492108HCID 68492108, compound

Product 1

HCID 68489206HCID 68489206, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-methoxymethoxy-5-dimethoxymethyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (3.34 g, 8.31 mmol) was dissolved in THF (100 mL), and the solution was treated with TMEDA (4.00 mL, 27.0 mmol), sec-butyl lithium-hexane solution (1.03 mol/L, 25.8 mL, 26.6 mmol) and iodine (3.16 g, 12.5 mmol), followed by purification by slurry using methanol and diisopropylether to obtain 4-methoxymethoxy-5-dimethoxymethyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (2.24 g, yield 51%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-29f6f6cbd88c4508bad6ca8f5c5e0647
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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