Water → HCID 15684608, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[2-(4-acetamido-3-hydroxyphenyl)-ethyl]-3,7-dimethylimidazo[1,2-a]pyridine (2.5 g) and phosphorus oxychloride (1.4 ml) in sulfolane (25 ml) was stirred for 1 hour at 100° C. The reaction mixture was added to a mixture of water and ethyl acetate and the separated aqueous layer was adjusted to pH 8 with potassium carbonate. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by a column chromatography on silica gel eluting with a mixture of chloroform and methanol (39:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was crystallized from a mixture of ethyl acetate and diethyl ether to give 6-[2-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-methylbenzoxazole (0.67 g).

Provenance & Evidence