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

HRID 1271546Notes

Reaction equation

HRID 1271546 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-912e9c4e51bc4a20949bfd3274941d9c
Source dataset
uspto-grants-2007_04
Patent number
US07205407B2

Reaction notes

Loading…