Iodobenzene → HCID 58042803, compound

HRID 564154Notes

Reaction equation

HRID 564154 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=2)[C:4](=[O:22])[CH:3]=1.I[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCOCC1.C(O)=O>[O:1]([C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=2)[C:4](=[O:22])[CH:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11575IodobenzeneHCID 58042802HCID 58042802, compound

Product 1

HCID 58042803HCID 58042803, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

To 100 mg (0.34 mmol) 4-hydroxy-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one (preparation 3) in 2.0 mL 1,4-dioxane is added 43 mg (0.39) potassium-tert-butylate and the mixture is stirred 30 min at RT. 77 μL (0.34 mmol) iodo-benzene and 21 mg (0.34 mmol) Cu-powder are added and the reaction mixture is stirred 5 h at 125° C. A few drops formic acid are added and after filtration the mixture is purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

Workup

  1. stirringthe reaction mixture is stirred 5 h at 125° C
  2. filtrationafter filtration the mixture
  3. customis purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

Sources & evidence

ORD record
ord-bd64e97ed44c48c8a6dd42d4761d183d
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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