Sulfuric Acid → Ethyl 8-bromo-6-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 931014Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][O-].[K+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>CC(O)C>[Br:1][C:2]1[C:3]2[N:4]([C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:9]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-bromo-5-methylpyridin-2-amine (3 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (7.6 g), sulfuric acid (0.86 mL) and 2-propanol (60 mL) was stirred at 90° C. for 24 hr. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1 g).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-3a5d69c5e2f0430bacd34e8c74462e02
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296746B2

Reaction notes

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