Iodine → 4-Chloro-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21245Notes

Reaction equation

HRID 21245 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([OH:23])[N:5]([C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:6]2=[O:13].CN(CCN(C)C)C.[I:32]I>C1COCC1>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:32])=[C:7]2[C:3]=1[CH:4]([OH:23])[N:5]([C:14]([CH3:15])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:22])[C:6]2=[O:13]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684933934-Chloro-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684892124-Chloro-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-chloro-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (300 mg, 0.904 mmol) was dissolved in THF (12 mL), and the solution was treated with TMEDA (0.30 mL, 2.0 mmol), sec-butyl lithium-hexane solution (1.01 mol/L, 2.0 mL, 2.0 mmol) and iodine (275 mg, 1.08 mmol), followed by purification by slurry using diisopropylether and hexane to obtain 4-chloro-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (350 mg, yield 85%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-c8fe6c7767bf48bfb48578ef0e270cfc
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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