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

HRID 1790056Notes

Reaction equation

HRID 1790056 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-77a3b44cb285441d922bff942b3398e8
Source dataset
uspto-grants-2006_07
Patent number
US07071208B2

Reaction notes

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