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

HRID 852221Notes

Reaction equation

HRID 852221 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-3f246d27dd7145319b2e8141e59286d5
Source dataset
uspto-grants-2007_08
Patent number
US07253181B2

Reaction notes

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