7-Chloroimidazo(1,2-a)pyridine → 7-Chloro-3-iodoimidazo[1,2-a]pyridine

HRID 1446655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446655
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[I:11]NC(=O)CCC(N)=O>C(#N)C>[I:11][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]2=[N:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 196959017-Chloroimidazo(1,2-a)pyridineHCID 21864724N-Iodosuccinamide

Produkt 1

HCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 7-chloro-imidazo[1,2,a]pyridine (6.10 g, 40 mmol) (Yamanaka, Motosuke et al., Chemical & Pharmaceutical Bulletin (1991), 39(6), 1556-67) in dry acetonitrile (100 mL), add N-iodosuccinamide. Stir for 30 minutes. Filter off the precipitate and then wash with acetonitrile. Recrystallize the precipitate from acetonitrile to give a white solid. Concentrate the filtrate, dilute with ethyl acetate, wash with 10% sodium hydrogensulfite (NaHSO3), saturated aqueous sodium bicarbonate, saturated aqueous NaCl, dry over MgSO4, filter and evaporate. Use the combined solid without further purification (8.0 g, 73%). 1H NMR (DMSO) δ 8.33 (d, 1H, J=7.3 Hz), 7.79 (d, 1H, J=2.0 Hz), 7.72 (s, 1H), 7.07 (dd, 1H, J=7.3 and 2.0 Hz).

Aufarbeitung

  1. filtrationFilter off the precipitate
  2. washwash with acetonitrile
  3. customRecrystallize the precipitate from acetonitrile
  4. customto give a white solid
  5. concentrationConcentrate the filtrate
  6. additiondilute with ethyl acetate
  7. washwash with 10% sodium hydrogensulfite (NaHSO3), saturated aqueous sodium bicarbonate, saturated aqueous NaCl
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. customevaporate
  11. customwithout further purification (8.0 g, 73%)

Quellen und Nachweise

ORD-Eintrag
ord-2640f52c4e004bb7a5929a2dd50be908
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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