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

HRID 645380

Reaction equation

Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][N:11]([CH3:19])[C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.C(O)C>COCCOC>[CH3:10][N:11]([CH3:19])[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:18]=2)[CH:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

215 μl of ethyl bromopyruvate are added to a suspension of 0.2 g of 5-dimethylaminopyridine-2-amine in 3 ml of DME. The reaction mixture is stirred at 20° C. for 16 hours, 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 comprising 15 g of silica, elution being carried out with a mixture of dichloromethane and methanol (98/2). The fractions comprising the expected product are combined and washed with a saturated sodium bicarbonate solution. The organic phase is dried and concentrated to dryness under reduced pressure to give 76 mg of ethyl 6-dimethylamino-imidazo[1,2-a]pyridine-2-carboxylate in the form of a green oil used as is in the continuation of the synthesis.

Workup

temperaturefor 16 hours at reflux
concentrationfinally, concentrated under reduced pressure
filtrationThe residue is filtered on a cartridge
wash15 g of silica, elution
additionbeing carried out with a mixture of dichloromethane and methanol (98/2)
washwashed with a saturated sodium bicarbonate solution
customThe organic phase is dried
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-638aea446ecf4c4e9f905d5163c291dd
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704989B2

Linked notes

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