Iodine → HCID 68490123, compound

HRID 21276Notes

Reaction equation

HRID 21276 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]([OH:25])[N:8]([C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:9]2=[O:15].CN(CCN(C)C)C.[I:34]I>C1COCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:11]([I:34])=[C:10]2[C:6]=1[CH:7]([OH:25])[N:8]([C:16]([CH3:17])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:24])[C:9]2=[O:15]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684937864-Methoxymethoxy-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 68490123HCID 68490123, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-methoxymethoxy-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.94 g, 8.61 mmol) was dissolved in THF (110 mL), and the solution was treated with TMEDA (4.20 mL, 27.8 mmol), sec-butyl lithium-hexane solution (0.95 mol/L, 29.0 mL, 27.6 mmol) and iodine (2.62 g, 10.3 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=4/1 to 7/3 to 6/4). The obtained solid was purified by slurry using hexane to obtain 4-methoxymethoxy-5-methyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (2.40 g, yield 60%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=4/1 to 7/3 to 6/4)
  2. customThe obtained solid was purified by slurry

Sources & evidence

ORD record
ord-633ec8009a6c499d8442696529d7dbc5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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