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

HRID 1784731Notes

Reaction equation

HRID 1784731 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(OCC)(=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-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Operations similar to Production Example 1-(2) were conducted using methyl 3-bromo-2-oxobutanoate and 2-amino-5-nitropyridine. The resulting solid was suspended in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to provide the title compound as yellow crystals.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution
  2. custompurified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-46262c6d7e1642fcbad221c17aa8a3f8
Source dataset
uspto-grants-2009_03
Patent number
US07504412B2

Reaction notes

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