Iodine → HCID 68492299, compound

HRID 21259Notes

Reaction equation

HRID 21259 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][O:13][CH3:14])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([OH:25])[N:5]([C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:6]2=[O:15].CN(CCN(C)C)C.[I:34]I>C1COCC1>[Cl:1][C:2]1[C:10]([O:11][CH2:12][O:13][CH3:14])=[CH:9][C:8]([I:34])=[C:7]2[C:3]=1[CH:4]([OH:25])[N:5]([C:16]([CH3:17])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:24])[C:6]2=[O:15]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 68491896HCID 68491896, compound

Product 1

HCID 68492299HCID 68492299, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-chloro-5-methoxymethoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (3.01 g, 8.32 mmol) was dissolved in THF (110 mL), and the solution was treated with TMEDA (4.00 mL, 26.5 mmol), sec-butyl lithium-hexane solution (0.95 mol/L, 28.0 mL, 26.6 mmol) and iodine (2.53 g, 9.98 mmol), followed by purification by slurry using diisopropylether to obtain 4-chloro-5-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (3.90 g, yield 96%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-2da3b087bec64fe8a891cff021616642
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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