Iodine → HCID 68492849, compound

HRID 21248Notes

Reaction equation

HRID 21248 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([OH:22])[N:5]([C:13]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[C:6]2=[O:12].CN(CCN(C)C)C.[I:31]I>C1COCC1>[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:31])=[C:7]2[C:3]=1[CH:4]([OH:22])[N:5]([C:13]([CH3:14])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:21])[C:6]2=[O:12]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684934234-Chloro-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 68492849HCID 68492849, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step. 3 of Example 16, 4-chloro-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (400 mg, 1.27 mmol) was dissolved in THF (16 mL), and the solution was treated with TMEDA (0.33 mL, 2.2 mmol), sec-butyl lithium-hexane solution (1.01 mol/L, 2.8 mL, 2.8 mmol) and iodine (387 mg, 1.52 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30) to obtain 4-chloro-5-methyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (352 mg, yield 63%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20 to 70/30)

Sources & evidence

ORD record
ord-9c4f0767ed55424bbd3d0a16a7c5bd1c
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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