Iodine → HCID 68492606, compound

HRID 21241Notes

Reaction equation

HRID 21241 reaction equation
[Cl:1][C:2]1[C:10]([F: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>[OH:22][CH:4]1[C:3]2[C:7](=[C:8]([I:31])[CH:9]=[C:10]([F:11])[C:2]=2[Cl:1])[C:6](=[O:12])[N:5]1[C:13]([CH3:14])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:21]

Participants

5

Reactant 3

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684908724-Chloro-3-hydroxy-5-fluoro-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 68492606HCID 68492606, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 3 of Example 16, 4-chloro-3-hydroxy-5-fluoro-2-(1-methyl-1-phenylethyl)isoindolinone (1.20 g, 3.75 mmol) was dissolved in THF (48 mL), and the solution was treated with TMEDA (2.30 mL, 15.0 mmol), sec-butyl lithium-hexane solution (1.01 mol/L, 15.0 mL, 15.0 mmol) and iodine (1.430 g, 5.63 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=80/20 to 70/30) to obtain 3-hydroxy-4-chloro-5-fluoro-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (830 mg, yield 50%).

Workup

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

Sources & evidence

ORD record
ord-4e40a6945db54f8c93e8f39bc594ee23
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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