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

HRID 1958473Notes

Reaction equation

HRID 1958473 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 67007442Ethyl 6,8-dibromoimidazo[1,2-a]pyridine-2-carboxylate hydrobromideYield 139.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4da1d85e7c554488b81c68906476d91f
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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