N-Iodosuccinimide → HCID 66986216, compound

HRID 1254027Notes

Reaction equation

HRID 1254027 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([I:27])C(=O)C1>CC#N.CCOC(C)=O>[I:27][C:9]1[NH:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][C:10]=1[C:12]1[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178509593HCID 178509593, compound

Product 1

HCID 66986216HCID 66986216, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 1 (700 mg, 2.85 mmol) was dissolved in 10 mL of MeCN, to which was added NIS (770 mg, 3.42 mmol) and catalytic amount of TPA. After stirring at rt overnight, the reaction was diluted with EtOAc, washed with aq NaHCO3, aq Na2S2O3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give 770 mg of 4-(5-iodo-2-phenyl-1H-imidazol-4-yl)benzonitrile. LCMS: [M+1]=372.

Workup

  1. washwashed with aq NaHCO3, aq Na2S2O3, water, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b9be2d97a78b4c86973495d10a63148a
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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