2-Amino-5-nitropyridine → Methyl 3-methyl-6-nitroimidazo[1,2-a]pyridine-2-carboxylate

HRID 230802Notes

Reaction equation

HRID 230802 reaction equation
Br[CH:2]([CH3:9])[C:3](=O)[C:4]([O:6][CH3:7])=[O:5].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1>C(O)C>[CH3:9][C:2]1[N:12]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 778882-Amino-5-nitropyridineHCID 11183175Methyl 3-bromo-2-oxobutanoate

Product 1

HCID 23120547Methyl 3-methyl-6-nitroimidazo[1,2-a]pyridine-2-carboxylateYield 23.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol suspension (400 mL) of methyl 3-bromo-2-oxobutyrate (46.6 g) and 2-amino-5-nitropyridine (33.3 g) was stirred at 90° C. for 24 hours. The precipitated solid was taken out through filtration, and the obtained solid was suspended in ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution, and purified through silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain methyl 3-methyl-6-nitroimidazo[1,2-a]pyridine-2-carboxylate (13.0 g) as a yellow crystal.

Workup

  1. filtrationThe precipitated solid was taken out through filtration
  2. washwashed with aqueous saturated sodium hydrogencarbonate solution
  3. custompurified through silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2d8ef7e6ce684813880ebfd636398915
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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