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

HRID 21096Notes

Reaction equation

HRID 21096 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[S: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[S: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 684924787-Amino-4-(thiophen-2-yl)isoindolinone

Product 1

HCID 684925757-Iodo-4-(thiophen-2-yl)isoindolinoneYield 44%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-(thiophen-2-yl)isoindolinone (212 mg, 0.920 mmol) was dissolved in acetonitrile (14.8 mL), and the solution was treated with potassium iodide (183 mg, 1.10 mmol), copper iodide (210 mg, 1.10 mmol), iodine (280 mg, 1.10 mmol) and tert-butyl nitrite (0.382 mL, 2.76 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile-6/1, chloroform/methanol=10/1) to obtain 7-iodo-4-(thiophen-2-yl)isoindolinone (138 mg, yield 44%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile-6/1, chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-94e234f08ab94670a8fba1d2b953f278
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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