N-Iodosuccinimide → 2-Chloro-3-iodopyrazolo[1,5-A]pyridine

HRID 530031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530031
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:18]=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1>C(#N)C>[Cl:9][C:10]1[C:18]([I:1])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 122844332-Chloropyrazolo[1,5-a]pyridine

Produkt 1

HCID 717433402-Chloro-3-iodopyrazolo[1,5-A]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-iodosuccinimide (1.06 g, 4.74 mmol) was added to a solution of 2-chloro-pyrazolo-[1,5-a]pyridine (27-2; 0.6 g, 3.95 mmol) in acetonitrile (18.0 mL). The resulting mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by silica gel flash chromatography (5-10% ethyl acetate in hexanes) provided the title compound. 1H NMR (400 MHz, CDCl3) δ 8.36-8.34 (d, J=6.8 Hz, 1 H), 7.40-7.37 (d, J=8.8 Hz, 1 H), 7.26-7.23 (m, 1 H), 6.84-6.81 (m, 1 H). MS (M+1): 279.0.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel flash chromatography (5-10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-026fe51dfcaf49f395c19ad0b857de4e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09351973B2

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