Ethyl bromopyruvate → Ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide

HRID 1958473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958473
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[BrH:1].[Br:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]2[N:4]([CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=2)[CH:5]=1

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 988513,5-Dibromo-2-pyridylamine

Produkt 1

HCID 67007442Ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromideAusbeute 139,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3,5-dibromopyridin-2-amine (2.51 g, 10 mmol) and ethyl 3-bromo-2-oxopropanoate (2.5 g, 13 mmol) in THF (50 mL) was heated at reflux 48 hrs. The solution was evaporated and the residue triturated with ether and the resulting solid was filtered and dried to give ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromide (3.0 g, 69% yield). LCMS (Conditions C): 2.70 min (RT); (M+H)+=347.09 (60%), 349.09 (100%), 351.08 (60%). 1H NMR, 400 MHz, CDCl3: δ 8.39 (d, 1.5 Hz, 1 H), 8.28 (s, 1 H), 7.67 (d, 1.5 Hz, 1 H), 4.46 (q, J=7.0 Hz, 2 H), 1.43 (t, J=7.0 Hz, 3 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux 48 hrs
  3. customThe solution was evaporated
  4. customthe residue triturated with ether
  5. filtrationthe resulting solid was filtered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4da1d85e7c554488b81c68906476d91f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410128B2

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