Ethyl bromopyruvate → 6-Tert-butyl 2-ethyl 5-chloro-7-methylimidazo[1,2-a]pyridine-2,6-dicarboxylate

HRID 1481961Notes

Reaction equation

HRID 1481961 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([Cl:16])[N:3]=1.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CCO>[Cl:16][C:4]1[N:3]2[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:1]=[C:2]2[CH:14]=[C:13]([CH3:15])[C:5]=1[C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 117631130Tert-butyl6-amino-2-chloro-4-methylnicotinate

Product 1

HCID 1176324636-Tert-butyl 2-ethyl 5-chloro-7-methylimidazo[1,2-a]pyridine-2,6-dicarboxylateYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 6-amino-2-chloro-4-methylnicotinate (9.4 g, 38.7 mmol, 1 equiv) and ethyl bromopyruvate (6.5 mL, 46.5 mmol, 1.2 equiv) in EtOH (194 mL) was heated to reflux for 2 h. Upon cooling to ambient temperature, the solution was concentrated in vacuo. The residue was triturated in ether and filtered to provide the product (11.4 g, 70%) as a cream colored solid. LCMS (ESI, M+1): 339.1.

Workup

  1. temperatureto reflux for 2 h
  2. concentrationthe solution was concentrated in vacuo
  3. customThe residue was triturated in ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fbfd72b06d094da282ec565b420b3032
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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