2-Aminopyridine → HCID 70818472, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the 80/20 mixture of 2-bromo-1-(3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one (19a) and 2-bromo-1-(3,4-dihydro-2H-1-benzopyran-8-yl)ethan-1-one (450 mg, 1.76 mmol) and 2-aminopyridine (166 mg, 1.76 mmol) in ethanol (10 mL) was heated at 60° C. overnight. The mixture was concentrated in vacuo. A 1M solution of sodium hydroxide (10 mL) and ethyl acetate (10 mL) were added. The aqueous layer was extracted with ethyl acetate (10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 40/60) to provide the desired imidazo-pyridine (19b) (228 mg, 0.91 mmol, 64%) as a beige solid.

Provenance & Evidence