Iodine → 7-Iodo-4-(furan-2-yl)isoindolinone

HRID 21093Notes

Reaction equation

HRID 21093 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:17].[K+].II.N(OC(C)(C)C)=O>C(#N)C.[Cu](I)I>[I:17][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 10906Tert-Butyl nitriteHCID 684927397-Amino-4-(furan-2-yl)isoindolinone

Product 1

HCID 684874877-Iodo-4-(furan-2-yl)isoindolinoneYield 58%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-(furan-2-yl)isoindolinone (43.0 mg, 0.201 mmol) was dissolved in acetonitrile (4.3 mL), and the solution was treated with potassium iodide (40.0 mg, 0.241 mmol), copper iodide (46.0 mg, 0.241 mmol), iodine (61.0 mg, 0.241 mmol) and tert-butyl nitrite (0.072 mL, 0.60 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=6/1) to obtain 7-iodo-4-(furan-2-yl)isoindolinone (37.8 mg, yield 58%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=6/1)

Sources & evidence

ORD record
ord-af72a1588c2f4fcfb3ce709ff335d054
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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