Ethanol → Ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate

HRID 600637

Reaction equation

[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(O)C>COCCOC>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:9]=2)[CH:8]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 0.2 g of 5-dimethylaminopyridine-2-amine in 3 mL of DME are added 215 μL of ethyl bromopyruvate. The reaction mixture is stirred at 20° C. for 16 hours and then, after addition of 3 mL of ethanol, for 16 hours at reflux, and finally concentrated under reduced pressure. The residue is filtered on a cartridge of 15 g of silica, eluting with a mixture of dichloromethane and methanol (98/2). The fractions containing the expected product are combined and washed with saturated sodium bicarbonate solution. The organic phase is dried and concentrated to dryness under reduced pressure to give 76 mg of ethyl 6-dimethylaminoimidazo[1,2-a]pyridine-2-carboxylate in the form of a green oil, which is used without further purification in the rest of the synthesis.

Workup

temperaturefor 16 hours at reflux
concentrationfinally concentrated under reduced pressure
filtrationThe residue is filtered on a cartridge of 15 g of silica
washeluting with a mixture of dichloromethane and methanol (98/2)
additionThe fractions containing the expected product
washwashed with saturated sodium bicarbonate solution
customThe organic phase is dried
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-b32fd19204cd4b839ca6f5a53c41e8d4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902219B2

Linked notes

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