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

HRID 914946Notes

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-4bb5992a8b584ae39367338add6887e4
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265127B2

Reaction notes

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