2-Bromopyridine → HCID 16678705, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromopyridine (1.0 g, 6.5 mmol) in THF (20 ml) was stirred at −78° C. in a nitrogen atmosphere. n-Butyllithium (8.1 ml 1.6M solution in hexanes, 13.0 mmol) was added and stirring at −78° C. was continued for 45 min. The resultant mixture was allowed to warm to 0° C. for two hours, in order to ensure completion of anion formation. The mixture was again cooled to −78° C. and compound 12a (0.5 g, 1.6 mmol) was added. After 30 min. the mixture was allowed to warm to 0° C. and saturated, aqueous ammonium chloride was added. The mixture was extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel using a mixture of petroleum ether and ethyl acetate (9:1) as the eluent. This afforded the desired product (0.15 g, 22%) as a yellowish gum. HRMS (ESI+): m/z=326.1305 [M+H]

Provenance & Evidence