2-Amino-3-benzyloxypyridine → 3-(2-Methyl-2-nitropropyl)-8-(phenylmethoxy)imidazo[1,2-a]pyridine

HRID 1271544Notes

Reaction equation

[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH:17]([CH2:20][C:21]([CH3:26])([N+:23]([O-:25])=[O:24])[CH3:22])[CH:18]=O>C(O)C>[CH3:22][C:21]([N+:23]([O-:25])=[O:24])([CH3:26])[CH2:20][C:17]1[N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:2]2=[N:1][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-amino-3-benzyloxypyridine (2.7 g, 13.5 mmol) and 2-bromo-4-methyl-4-nitropentanal (3.0 g, 13.5 mmol) in ethanol (20 ml) is heated at 100° C. overnight. The solvent is removed under reduced pressure and the residue is treated with saturated aqueous NaHCO3 solution. The aqueous mixture is extracted two times with ethyl acetate. The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed (silica gel, dichloromethane/ethanol 9:1) to give 2.83 g of 3-(2-methyl-2-nitropropyl)-8-(phenylmethoxy)imidazo[1,2-a]pyridine (64%).

Workup

customThe solvent is removed under reduced pressure
additionthe residue is treated with saturated aqueous NaHCO3 solution
extractionThe aqueous mixture is extracted two times with ethyl acetate
dry with materialThe combined organic extracts are dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue is chromatographed (silica gel, dichloromethane/ethanol 9:1)

Sources & evidence

ORD record: ord-aecf931daf5b452495cf6d332b9d36c6
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205407B2

Reaction notes

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