Acetic Acid → 2-Ethyl-3-iodopyrazolo[1,5-a]pyridine

HRID 408801

Reaktionsgleichung

Reaktionsgleichung von HRID 408801
[CH2:1]([C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].C(O)(=O)C.[I:16]N1C(=O)CCC1=O>>[CH2:1]([C:3]1[C:11]([I:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 161162612-Ethylpyrazolo[1,5-a]pyridine

Produkt 1

HCID 161149332-Ethyl-3-iodopyrazolo[1,5-a]pyridineAusbeute 93 %

Versuchsvorschrift

2-Ethylpyrazolo[1,5-a]pyridine (4.1 g, 22 mmol) was stirred in acetic acid (2.6 g, 18 mmol) and N-iodosuccinimide (8 g, 40 mmol) was added in portions over 5 hrs. The mixture was evaporated and purified on silica gel with ethyl acetate in hexanes (0-15%) to give the desired compound (4.5 g, 93%). LCMS for C9H10N2 (M+H)+: m/z=273.1. 1H NMR (300 MHz, DMSO-d6): δ 8.62 (m, 1H), 7.40 (m, 1H), 7.27 (m, 1H), 6.82 (m, 1H), 2.72 (m, 2H), 1.22 (m, 3H).

Aufarbeitung

  1. customThe mixture was evaporated
  2. custompurified on silica gel with ethyl acetate in hexanes (0-15%)

Quellen und Nachweise

ORD-Eintrag
ord-30e655346d30462eaaa059ffa8808f22
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759359B2

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