Water → 7-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

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Reaction Steps

Added ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (15 g, 56 mmol) and lithium hydroxide monohydrate (3 g, 71.4 mmol) into tetrahydrofuran/ethanol/water (1:2:1, 560 mL total) solution. After stirring at ambient temperature overnight, the solvent was removed under vacuum to give a yellow gum. Water (300 mL) and dichloromethane was added, and the phases were separated. The aqueous layer was cooled in an ice-water bath before adjusting the pH to 3 using 2N sulfuric acid. The product precipitated out and was collected by filtration and washed with a small amount of water (50 mL) before drying under vacuum to give 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid as an off-white solid (8.3 g).

Provenance & Evidence