N-Iodosuccinimide → HCID 68543035, compound

HRID 1446657Notes

Reaction equation

HRID 1446657 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[CH:14][N:15]=[C:9]2[CH:8]=1.C1C(=O)N([I:23])C(=O)C1>C(O)C.C(OCC)(=O)C>[I:23][C:13]1[N:10]2[CH:11]=[CH:12][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][C:9]2=[N:15][CH:14]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 21620216HCID 21620216, compound

Product 1

HCID 68543035HCID 68543035, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 7-pyridin-2-yl-imidazo[1,2-a]pyridine (0.3 g, 1.5 mmol) in absolute ethanol (10 mL) and add NIS (0.35 g, 1 equiv.). Heat the reaction to 50° C. for 30 minutes under N2 then dilute with ethyl acetate. Wash the organic layer with 1 N NaOH followed by sat NaCl. Dry the organic layer over magnesium sulfate, filter and concentrate to give a light tan solid (0.4 g, 82%). MS (ES), m/z 322 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction to 50° C. for 30 minutes under N2
  3. washWash the organic layer with 1 N NaOH
  4. dry with materialDry the organic layer over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-2ab9a316f07e4bf6b08b24dc47082c13
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…