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

HRID 914949Notes

Reaction equation

HRID 914949 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-d023462a7e094c9fa4a86843a251fcab
Source dataset
uspto-grants-2007_09
Patent number
US07265127B2

Reaction notes

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