2-Amino-5-methoxypyridine → 3-(2-Methyl-2-nitropropyl)-6-methoxyimidazo[1,2-a]pyridine

HRID 1294596Notes

Reaction equation

HRID 1294596 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.Br[CH:11]([CH2:14][C:15]([CH3:20])([N+:17]([O-:19])=[O:18])[CH3:16])[CH:12]=O>ClCCl>[CH3:16][C:15]([N+:17]([O-:19])=[O:18])([CH3:20])[CH2:14][C:11]1[N:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]2=[N:1][CH:12]=1

Participants

4

Reactant 2

HCID 113209342-Amino-5-methoxypyridineHCID 220385582-Bromo-4-methyl4-nitropentanal

Product 1

HCID 220385743-(2-Methyl-2-nitropropyl)-6-methoxyimidazo[1,2-a]pyridineYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-methoxypyridine (J. Med. Chem., 24:39, 1981; 2.02 g, 16.3 mmol) and 2-bromo-4-methyl-4-nitropentanal (16.3 mmol) are reacted as described in Amine 7 and the product is isolated in two crops from the concentrated mixture by heating twice with dichloromethane (30 ml and 10 ml) and filtration without further chromatographic purification to give 1.71 g of 3-(2-methyl-2-nitropropyl)-6-methoxyimidazo[1,2-a]pyridine (42%).

Workup

  1. customthe product is isolated in two crops from the concentrated mixture

Sources & evidence

ORD record
ord-5f7b4eaac57242d28f105ec11bacf00c
Source dataset
uspto-grants-2007_07
Patent number
US07241772B2

Reaction notes

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