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

HRID 931029Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([F: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]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-bromo-5-fluoropyridin-2-amine (3.0 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (7.4 g), sulfuric acid (0.84 mL) and 2-propanol (60 mL) was heated at 90° C. for 3 days. 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 suspended in ethanol, and the obtained solid was collected by filtration to give the title compound (3.6 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
filtrationthe obtained solid was collected by filtration

Sources & evidence

ORD record: ord-274cae4ade9d4bb0942a75ff09bcd3bf
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296746B2

Reaction notes

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