2-Amino-5-methoxypyridine → 3-(2-Methyl-2-nitropropyl)-6-methoxyimidazo[1,2-a]pyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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%).